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研究生:目那
研究生(外文):Yogesh Munot
論文名稱:1.歧狀高分子鍵結生化感應器2.氧金屬錯合物催化有氧性氧化反應
論文名稱(外文):1. Synthesis of Dendritic Bioprobes 2. Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions
指導教授:陳建添陳建添引用關係
指導教授(外文):Chien-Tien Chen
學位類別:博士
校院名稱:國立臺灣師範大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
畢業學年度:94
語文別:英文
論文頁數:400
中文關鍵詞:Aerobic oxidationBioprobedendrimer
外文關鍵詞:有氧性氧化生物偵檢歧狀高分子
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Thesis Title

“Synthesis of Dendritic Bioprobes and Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions”
Thesis is divided into two chapters.
Chapter-I: Synthesis of Dendritic Bioprobes.
Chapter-II: Catalysis of Oxometallic species in Asymmetric Reactions and Nucleophilic Acyl Substitutions.
Chapter-I: Synthesis of Dendritic Bioprobes
This chapter is further divided into six sections.
Section 1: Nucleation of Au nanoparticles or ZnS/CdSe quantum dots inside the cage of organic ligand by Ring closing metathesis (RCM)
This section describes the stabilization strategy for Au nanoaprticles and CdSe/ZnS QDs by new netting process to efficiently lock Au or ZnS/CdSe nanoparticles (Scheme 1)
Scheme-1

in central core. The netting unit 2 was prepared from intermediate 1. Methyl gallate by benzylation with benzylbromide in the presence of a base K2CO3, subsequent double allylation with allyl bromide and K2CO3 gives the intermediate 1. The methyl ester was saponified in MeOH followed by the amidation gives required unit 2. The thiolate end in 2 for priming to the pyridine stabilized CdSe/ZnS or HAuCl4 in presence of NaBH4. The allyloxy units at both C3 and C5 positions of 2 were used for netting and corss-linking by ring closing metathesis by Grubb’s catalyst.1 The stabilization strategy presented here may be extended to be extended to other colloidal systems.

Section 2: Synthesis of biocompatible water-soluble pentaol or haxaol coated ZnS/CdSe shell/core type semiconductor quantum dots as fluorescent biological labels
Functionalized N-2-mercaptoethyl-gallamides bearing five2 or six hydroxyl units that are tethered with diethylene glycol ether(s) allow for transferring hydrophobically pyridine-

Scheme 2

capped ZnS/CdSe shell/core nanoparticles from an organic to an aqueous layer with intact fluorescent profiles. The required dendritic polyol units 6 (Scheme 2) or 10 (Scheme 3) were prepared from 5 or 9 by osmium catalyzed dihydroxylation respectively.

Scheme-3


Dendritic Nanohybrids in Proteomics

[Fig. 1: Sample: total protein of E. coli BL21(DE3) Protein extraction : acetone precipitate Protein conc. : 9.48 mg/mL Gel conc. : SDS-PAGE 12.5% Electrophoresis time : 80 min (at 100V)]
Subsequent unmasking of S-trityl group by TFA/Et3SiH, encapsulate the pyridine-stabilized ZnS/CdSe shell/core type quantum dots. The resultant bioprobes are very stable, water-soluble, dispersive, and narrowly distributed in size. The nanohybrids were studied in proteomics (Fig. 1). After endocytic uptake of nanohybrids, HeLa cancer cells were stably labeled for two days with no detectable effects on cell morphology or physiology. Notabley, we saw no discernible fluorescence loss of the QD labels: brightly fluorescent cells were visible during the entire imaging sequence (Fig. 2). This indicates QDs were taken up by the cells via endocytosis.3

Cellular Imaging studies

Fig. 2: Distribution of Penta-podal QDs in live HeLa cells. Uptake and transport of QDs with 10µL solution. The image Epifluorescence and confocal microscope image of cells 12 hours after being spontaneous uptake by cells.

Section 3: Hybridization of Gallactoside-capped gallamide Dendrons with CdSe/ZnS Core/Shell nanoparticles: Fluorescent, Nucleus Localization probes for Cancer cells
Mostly monomeric-carbohydrates are attached to nanoparticles.4 Moreover; the application of dendritic carbohydrate–conjugated quantum dots in biological assays has not been explored. This is the first example of dendritic gallactoside dendrimer ligand anchored to ZnS/CdSe quantum dots. The simple and convenient method for the construction of dendritic gallactoside gallamide ligand encapsulated CdSe/ZnS quanum dots. The key chemical transformation which allows facile synthesis of this dendritic ligand (15) from 14, is the copper (I)-catalyzed azide–alkyne cycloaddition, a click reaction.5a (Scheme 4). The 13 is readily prepared from methyl gallate by treatment with 12 in presence of K2CO3 in refluxed acetonitrile. The resultant bioprobes 16 are very stable, water-soluble, dispersive, and narrowly distributed in size, which might be of great potential for the investigation of the biofunctions of carbohydrates.5b

Scheme-4








16






Fig. 3: Distribution of nanohybrid-16 in COS-7 kidney cancer cells and A549 liver cancer cells.

Section 4: Dendritic crown ether-capped ZnS/CdSe Core/Shell nanoparticles: Potential fluorescent bioprobes to study the Transmembrane Profiles
The novel 12-crown-4 dendritic ligand 17 was prepared via Cu(I) catalysed Click chemistry from 14. Funcationalization of ZnS/CdSe QDs with 12-crwon-4 dendritic ligand has achieved,6 to investigate the multiple binding studies with Li+ ions in H2O.7 When treated with kidney cancer cells, the nanohybrid-18 induce facile endocytic uptake, which opens up a new entry in the field of cell-biology for studying dynamic transmembrane behaviors.
Scheme-5


18











Fig. 4: Distribution of nanohybrid-18 in live COS-7 cells. Uptake and transport of QDs with 10µL solution.

Section 5: Doubly Ortho-linked Quinoxaline and 3/4-diarylaminopyridine Hybrid as Donor-type Optoelectronic Capping Materials for ZnS/CdSe shell/core nanocrystals
Using Nitrogen donars as binding group, we have created monomeric Q-pyridine –CdSe/ZnS nanocrystal complexes. The new design allows the simple synthesis of surfactant 21 and 22 by Palladium catalyzed coupling reaction of 20 (Q-H)8 with 4-bromo pyridine or 3-bromo pyridine respectively (Scheme 6). The single crystal structures and optoelectronic properties of Q-H-py wrapped ZnS/CdSe nanohybrids are promising for application9 in OLEDs and photovoltaic cells.10


Scheme-6






Section 6: Hydrophobic Nanocrystals coated with Amphiphilic Tetraol and Tetraphosphonic and Tetra carboxylic acid: A general route to water soluble CdSe/ZnS and Pd nanoparticles
We have developed a simple synthetic method for preparation of tetraol (24) or tetraacid (25 or 26) dendritic ligand from 23. This can be used to transfer various nanoparticles11

Scheme-7

from organic solvents to water. The aqueous nanoparticles have physical properties and reactivities similar to those in organic solvents. The wrapping such type of gallamide dendritic ligand around Pd nanoparticles may further enhance the stability.12 The Pd nanoparticles could be useful for C-C bond formation reaction like as Suzuki reaction, Heck coupling.

Chapter-II: Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions
This chapter is further divided into two sections.
Section 1: Direct Atom-Efficient Esterification between Carboxylic Acids and Alcohols Catalyzed by Amphoteric, Water-Tolerant TiO(acac)2
The esterification of carboxylic acids with different functionalized alcohols is one of the most important and commonly used transformations in organic synthesis. A diverse array of oxometallic species were examined as catalysts for a test direct condensation of benzoic acid and 2-phenylethanol in 1:1 stoichiometry. Besides Group IVB MOCl2-xH2O and TiOX2-xH2O, Group VB VOCl2-xTHF and Group IVB TiO(acac)2 were found to be

Scheme-8



the most efficient and water-tolerant catalysts for the test reaction. The new neutral catalytic protocol with the optimal TiO(acac)2, tolerates many stereo/electronic structural variations in both (di)acid (1o-3o alkyl and aryl) and (di)alcohol (1o, 2o alkyl, and aryl) components with high chemoselectivity.13

Section 2: Synthesis of Dendrimer catalysts and it’s application towards catalysis and also for DNA cleavage
We demonstrate for the first time use of oxo-metallic species in dendrimer catalyst. This is simple and convenient method for the construction of dendritic gallamide catalyst. The key chemical transformation which allows facile synthesis of this dendritic ligand (29 or 30) from 28, is the copper (I)-catalyzed azide–alkyne cycloaddition, a click reaction.5a (Scheme 10). To check the feasibility of enhanced reactivity in a dendritic catalyst resulting from cooperative reactivity between catalytic units. Further exploration and optimization of such multimeric catalysts in related asymmetric reactions are ongoing.
The titled vanadyl(V) complexes14 serve as efficient reagents for cleaving supercoiled plasmid DNA by photoinitiation.15 We have shown the vanadyl Complexes, derived from 2-hydroxy-1-naphthaldehyde and L-phenylalanine, exhibits a unique wedge feature, inducing a site-selective photocleavage at the C22- T23 of the bulge backbone for a HIV-27 DNA system at 0.15 íM. Transient absorption experiments for corresponding Vanadyl complex indicate the involvement of LMCT with concomitant tautomerization, leading to an o-quinone-methide V-bound hydroxyl species responsible for the cleavage profiles. The use of dendrimer-Vanadyl complex for such DNA cleavage is underway.

Scheme 9


Scheme 10



Scheme-11
Thesis Title

“Synthesis of Dendritic Bioprobes and Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions”
Thesis is divided into two chapters.
Chapter-I: Synthesis of Dendritic Bioprobes.
Chapter-II: Catalysis of Oxometallic species in Asymmetric Reactions and Nucleophilic Acyl Substitutions.
Chapter-I: Synthesis of Dendritic Bioprobes
This chapter is further divided into six sections.
Section 1: Nucleation of Au nanoparticles or ZnS/CdSe quantum dots inside the cage of organic ligand by Ring closing metathesis (RCM)
This section describes the stabilization strategy for Au nanoaprticles and CdSe/ZnS QDs by new netting process to efficiently lock Au or ZnS/CdSe nanoparticles (Scheme 1)
Scheme-1

in central core. The netting unit 2 was prepared from intermediate 1. Methyl gallate by benzylation with benzylbromide in the presence of a base K2CO3, subsequent double allylation with allyl bromide and K2CO3 gives the intermediate 1. The methyl ester was saponified in MeOH followed by the amidation gives required unit 2. The thiolate end in 2 for priming to the pyridine stabilized CdSe/ZnS or HAuCl4 in presence of NaBH4. The allyloxy units at both C3 and C5 positions of 2 were used for netting and corss-linking by ring closing metathesis by Grubb’s catalyst.1 The stabilization strategy presented here may be extended to be extended to other colloidal systems.

Section 2: Synthesis of biocompatible water-soluble pentaol or haxaol coated ZnS/CdSe shell/core type semiconductor quantum dots as fluorescent biological labels
Functionalized N-2-mercaptoethyl-gallamides bearing five2 or six hydroxyl units that are tethered with diethylene glycol ether(s) allow for transferring hydrophobically pyridine-

Scheme 2

capped ZnS/CdSe shell/core nanoparticles from an organic to an aqueous layer with intact fluorescent profiles. The required dendritic polyol units 6 (Scheme 2) or 10 (Scheme 3) were prepared from 5 or 9 by osmium catalyzed dihydroxylation respectively.

Scheme-3


Dendritic Nanohybrids in Proteomics

[Fig. 1: Sample: total protein of E. coli BL21(DE3) Protein extraction : acetone precipitate Protein conc. : 9.48 mg/mL Gel conc. : SDS-PAGE 12.5% Electrophoresis time : 80 min (at 100V)]
Subsequent unmasking of S-trityl group by TFA/Et3SiH, encapsulate the pyridine-stabilized ZnS/CdSe shell/core type quantum dots. The resultant bioprobes are very stable, water-soluble, dispersive, and narrowly distributed in size. The nanohybrids were studied in proteomics (Fig. 1). After endocytic uptake of nanohybrids, HeLa cancer cells were stably labeled for two days with no detectable effects on cell morphology or physiology. Notabley, we saw no discernible fluorescence loss of the QD labels: brightly fluorescent cells were visible during the entire imaging sequence (Fig. 2). This indicates QDs were taken up by the cells via endocytosis.3

Cellular Imaging studies

Fig. 2: Distribution of Penta-podal QDs in live HeLa cells. Uptake and transport of QDs with 10µL solution. The image Epifluorescence and confocal microscope image of cells 12 hours after being spontaneous uptake by cells.

Section 3: Hybridization of Gallactoside-capped gallamide Dendrons with CdSe/ZnS Core/Shell nanoparticles: Fluorescent, Nucleus Localization probes for Cancer cells
Mostly monomeric-carbohydrates are attached to nanoparticles.4 Moreover; the application of dendritic carbohydrate–conjugated quantum dots in biological assays has not been explored. This is the first example of dendritic gallactoside dendrimer ligand anchored to ZnS/CdSe quantum dots. The simple and convenient method for the construction of dendritic gallactoside gallamide ligand encapsulated CdSe/ZnS quanum dots. The key chemical transformation which allows facile synthesis of this dendritic ligand (15) from 14, is the copper (I)-catalyzed azide–alkyne cycloaddition, a click reaction.5a (Scheme 4). The 13 is readily prepared from methyl gallate by treatment with 12 in presence of K2CO3 in refluxed acetonitrile. The resultant bioprobes 16 are very stable, water-soluble, dispersive, and narrowly distributed in size, which might be of great potential for the investigation of the biofunctions of carbohydrates.5b

Scheme-4








16






Fig. 3: Distribution of nanohybrid-16 in COS-7 kidney cancer cells and A549 liver cancer cells.

Section 4: Dendritic crown ether-capped ZnS/CdSe Core/Shell nanoparticles: Potential fluorescent bioprobes to study the Transmembrane Profiles
The novel 12-crown-4 dendritic ligand 17 was prepared via Cu(I) catalysed Click chemistry from 14. Funcationalization of ZnS/CdSe QDs with 12-crwon-4 dendritic ligand has achieved,6 to investigate the multiple binding studies with Li+ ions in H2O.7 When treated with kidney cancer cells, the nanohybrid-18 induce facile endocytic uptake, which opens up a new entry in the field of cell-biology for studying dynamic transmembrane behaviors.
Scheme-5


18











Fig. 4: Distribution of nanohybrid-18 in live COS-7 cells. Uptake and transport of QDs with 10µL solution.

Section 5: Doubly Ortho-linked Quinoxaline and 3/4-diarylaminopyridine Hybrid as Donor-type Optoelectronic Capping Materials for ZnS/CdSe shell/core nanocrystals
Using Nitrogen donars as binding group, we have created monomeric Q-pyridine –CdSe/ZnS nanocrystal complexes. The new design allows the simple synthesis of surfactant 21 and 22 by Palladium catalyzed coupling reaction of 20 (Q-H)8 with 4-bromo pyridine or 3-bromo pyridine respectively (Scheme 6). The single crystal structures and optoelectronic properties of Q-H-py wrapped ZnS/CdSe nanohybrids are promising for application9 in OLEDs and photovoltaic cells.10


Scheme-6






Section 6: Hydrophobic Nanocrystals coated with Amphiphilic Tetraol and Tetraphosphonic and Tetra carboxylic acid: A general route to water soluble CdSe/ZnS and Pd nanoparticles
We have developed a simple synthetic method for preparation of tetraol (24) or tetraacid (25 or 26) dendritic ligand from 23. This can be used to transfer various nanoparticles11

Scheme-7

from organic solvents to water. The aqueous nanoparticles have physical properties and reactivities similar to those in organic solvents. The wrapping such type of gallamide dendritic ligand around Pd nanoparticles may further enhance the stability.12 The Pd nanoparticles could be useful for C-C bond formation reaction like as Suzuki reaction, Heck coupling.

Chapter-II: Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions
This chapter is further divided into two sections.
Section 1: Direct Atom-Efficient Esterification between Carboxylic Acids and Alcohols Catalyzed by Amphoteric, Water-Tolerant TiO(acac)2
The esterification of carboxylic acids with different functionalized alcohols is one of the most important and commonly used transformations in organic synthesis. A diverse array of oxometallic species were examined as catalysts for a test direct condensation of benzoic acid and 2-phenylethanol in 1:1 stoichiometry. Besides Group IVB MOCl2-xH2O and TiOX2-xH2O, Group VB VOCl2-xTHF and Group IVB TiO(acac)2 were found to be

Scheme-8



the most efficient and water-tolerant catalysts for the test reaction. The new neutral catalytic protocol with the optimal TiO(acac)2, tolerates many stereo/electronic structural variations in both (di)acid (1o-3o alkyl and aryl) and (di)alcohol (1o, 2o alkyl, and aryl) components with high chemoselectivity.13

Section 2: Synthesis of Dendrimer catalysts and it’s application towards catalysis and also for DNA cleavage
We demonstrate for the first time use of oxo-metallic species in dendrimer catalyst. This is simple and convenient method for the construction of dendritic gallamide catalyst. The key chemical transformation which allows facile synthesis of this dendritic ligand (29 or 30) from 28, is the copper (I)-catalyzed azide–alkyne cycloaddition, a click reaction.5a (Scheme 10). To check the feasibility of enhanced reactivity in a dendritic catalyst resulting from cooperative reactivity between catalytic units. Further exploration and optimization of such multimeric catalysts in related asymmetric reactions are ongoing.
The titled vanadyl(V) complexes14 serve as efficient reagents for cleaving supercoiled plasmid DNA by photoinitiation.15 We have shown the vanadyl Complexes, derived from 2-hydroxy-1-naphthaldehyde and L-phenylalanine, exhibits a unique wedge feature, inducing a site-selective photocleavage at the C22- T23 of the bulge backbone for a HIV-27 DNA system at 0.15 íM. Transient absorption experiments for corresponding Vanadyl complex indicate the involvement of LMCT with concomitant tautomerization, leading to an o-quinone-methide V-bound hydroxyl species responsible for the cleavage profiles. The use of dendrimer-Vanadyl complex for such DNA cleavage is underway.
Chapter I. Synthesis of Dendritic Bioprobes

Section 1: Nucleation of Au nanoparticles or CdSe/ZnS quantum dots inside the cage of organic ligand by Ring closing metathesis (RCM)
1.1.1 Introduction 1
1.1.2 Background 6
1.1.3 Research Goals 9
1.1.4 Results 11
1.1.5 Conclusion 19
1.1.6 Future work 20

Section 2: Synthesis of biocompatible water-soluble pentaol or haxaol coated CdSe/ZnS semiconductor quantum dots as fluorescent biological labels
1.2.1 Introduction and Background 22 1.2.2 Research Goals 28
1.2.3 Results 28
1.2.4 Application of Nanohybrides 36
1.2.5 Conclusion 39

Section 3: Hybridization of Gallactoside-capped gallamide Dendrons with CdSe/ZnS Core/Shell nanoparticles: Fluorescent, Nucleus Localization probes for Cancer cells
1.3.1 Introduction and Background 40 1.3.2 Research Goals 44
1.3.3 Results 45
1.3.4 Application of Nanohybrides 53
1.3.5 Conclusion 56


Section 4: Dendritic crown ether-capped ZnS/CdSe Core/Shell nanoparticles: Potential fluorescent bioprobes to study the Transmembrane Profiles
1.4.1 Introduction 57
1.4.2 Background 59
1.4.3 Research Goals 61
1.4.4 Results 62
1.4.5 Application of Nanohybrides 67
1.4.6 Conclusion 68
1.4.7 Future Plan 69

Section 5: Doubly Ortho-linked Quinoxaline and 3/4-diarylaminopyridine Hybrid as Donor-type Optoelectronic Capping Materials for ZnS/CdSe shell/core nanocrystals
1.5.1 Introduction and Background 70 1.5.2 Research Goals 73
1.5.3 Results 74
1.5.4 Conclusion 82

Section 6: Hydrophobic Nanocrystals coated with Amphiphilic Tetraol and Tetraphosphonic and Tetra carboxylic acid: A general route to water soluble CdSe/ZnS and Pd nanoparticles
1.6.1 Introduction 83
1.6.2 Background 84
1.6.3 Research Goals 91
1.6.4 Results 92
1.6.5 Conclusion 95

Chapter-II: Catalysis of Oxometallic species in Aerobic Oxidation and Nucleophilic Acyl Substitutions
Section 1: Direct Atom-Efficient Esterification between Carboxylic Acids and Alcohols Catalyzed by Amphoteric, Water-Tolerant TiO(acac)2
2.1.1 Introduction 96
2.1.2 Background 98
2.1.3 Research Goals 103
2.1.4 Results 104
2.1.5 Conclusion 109

Section 2: Synthesis of Chiral N-salicylidene vanadyl carboxylate Oxo-Vandium Dendritic Catalyst and its application towards asymmetric catalysis and DNA Photocleavage
2.2.1 Introduction 110
2.2.2 Background 116
2.2.3 Our laboratory Work 118
2.2.4 Research Goals 122
2.2.5 Results 122
2.2.6 Applications in Asymmetric Catalysis 126 2.2.7 Conclusion 128
2.2.8 Future Plan 129

References 130
Experimental Section 142
Appendix 1H NMR, 13C NMR, Data of Synthesized Compounds 153
References

1. (a) Wedland, M. S.; Zimmerman, S.C. J. Am. Chem. Soc. 1999, 121, 1389. (b) Guo,
W.; Li, J. J.; Wang, Y. A.; Peng, X. J. Am. Chem. Soc. 2003, 125, 3901.
2. Chen, C.-T.; Pawar, V. D.; Munot, Y. S.; Chen, C.-C.; Hsu, C.-J. Chem. Commun.
2005, 2483.
3. (a) Bruchez, M.;mMoranne, M.; Gin, P. ; Weiss, Alivisatos, A. P.; Science, 1998, 281,
2013. (b) Chan, W. C.; Nie, S. M. Science, 1998, 281, 2016.
4. (a) Chen, Y.; Ji, T.; Rosenwig, Z, Nano. Lett. 2003, 3, 581; (b) Osaki, F.; Kanamori,
T.; Sando, S.; Sera, T.; Aoyama, Y., J. Am. Chem. Soc. 2004, 126, 6520; (c) Xie, M.;
Liu, H. –H.; Chen, P.; Zhang, Z. –L.; Wang, X. –H.; Xie, Z. -X.; Du, Y. –M.; Pan, B.
–Q.; Pang, D. W. Chem. Commun. 2005, 5518. (d) A. G. Barrientos, A. G. ; De la.
Fuente, J. M. ; Rojas, T. S. ; Fernandez, A.; Penades, S. Chem. Eur. J. 2003, 9, 1909.
(e) Lin, C. C. ; Yah, Y. –C. ; Yang, C. –Y. ; Chen, C.-L. ; Chen, G. –F. ; Chen, C. –
C, ; Wu, Y. –C. J. Am. Chem. Soc. 2002, 124, 3508.
5. (a) Z. P. Demko and K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2113. (b) to be
communicated 2006.
6. (a) Chen, C. -Y.; Cheng, C. -T.; Lai, C. -W.; Wu, P. -W.; Wu. K.-C.; Chou, P.-T.;
Chou, Y.-H.; Chiu, H.-T. Chem Commun. 2006, 263 .(b) Lin, S. Y., Liu, S. W. Lin, C.
M. Chen, C.H. Anal Chem. 2002, 74, 330.
7. to be communicated.
8. Chen, C.-T.; Lin, J.-S.; Moturu, V. R. K. Murthy.: Lin, Y. –W.; Yi, W.; Tao, Y.-T.;
Chein, C. –H. Chem. Commun. 2005, 31, 3980.
9. (a) Milliron, D. J; Alivisatos, A.. P.; Pitois, C.; Edder, C.; Frechet, J. M. J. Advan.
Mater. 2003, 12, 58. (b) Huynh, W. U.; Peng, X.; Alivisatos, A. P. Adv. Mater. 1999,
11, 923. (c) Geenham, N. C.; Peng, X.; Alivisatos, A. P. Phys Rev. B 1996, 54, 17628
10. to be communicated.
11. (a) Kim, S. –W.; Kim, S.; Tracy, J. B.; Jasanoff, A.; Bawendi, M. G. J. Am. Chem.
Soc. 2005, 127, 4556. (b)
12. (a) Bruce, J. I.; Chanbron, J.-C.; Koll, P.; Sauvage, J.-P. J. Chem.Soc., Perkin Trans.
1 2002, 1226. (b) Kaes, C.; Hosseini, M. W.; De Cian, A.; Fischer, J. Tetrahedron
Lett. 1997, 38, 3901. (c) Mendoza, J.; Mesa, E.; Rodriguez-Ubis, J.; Vasquez, P.;
Vogtle, F.; Windschief, P.; Rissanen, K.; Lehn, J.-M.; Lilienbaum, P.; Ziessel, R.
Angew. Chem. Int. Ed. Engl. 1991, 30, 1331. (d) Romero, F. M.; Ziessel, R.
Tetrahedron Lett. 1994, 5, 9203. (e) Baxter, P. N. M. J. Org. Chem. 2000, 65, 1257.
(f) to be communicated.
13. (a) Chen, C.-T.; Kuo, J.-H.; Ku, C.-H.; Weng, S.-S.; Liu, C.-Y. J. Org. Chem.
2005, 70, 1328. (b) Chen, C. –T.; Munot, Y. S. J. Org. Chem. 2005, 70, 8625
14. (a) Radodevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
(b) Weng, S. –S.; Shen, M. –W.; Kao, J. –Q.; Munot, Y. S. Chen, C. –T. Proc. Natl.
Acad. Sci. USA, 2006, 103, 3522.(c) Chen, C.-T.; Kuo, J.-H.; Pawar, V. D.; Munot,
Y. S.; Weng, S.-S.; Ku, C.-H.; Liu, C.-Y. J. Org. Chem. 2005, 70, 1188.
15. (a) Chen, C.-T.; Lin, J.-S.; Kuo, J.-H.; Weng, S.-S.; Cuo, T.-S.; Lin, Y.-W.; Cheng,
C.-C.; Huang, Y.-C.; Yu, J.-K.; Chou, P.-T. Org. Lett. 2004, 6, 4471. (b) Hon, S.-W.;
Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett.
2001, 3, 869. (c) Barhate, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529. (d) Annis, D.
A.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 707.
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