臺灣博碩士論文加值系統

詳見英文摘要

In this thesis, several new nickel-catalyzed cyclization and coupling reactions and their application in organic synthesis are discussed in detail. For convenience and better clarity, the thesis is divided in to six chapters. The first two chapters deal with the synthesis of coumarin derivatives, the third chapter depicts the synthesis of indenols via carbocyclization, fourth chapter describes about the synthesis of medium-size ring lactones and synthesis of 1,2-dihydroarenes is discussed in last two chapters.
The nickel-catalyzed cyclization of 7-oxabenzonorbornadienes with alkyl propiolates is investigated in the chapter 1. The reaction of 7-oxabenzonorbornadienes with alkyl propiolates catalyzed by nickel complexes gave benzocoumarin derivatives in high yields with high regio- and stereoselectivity. The catalytic mechanism for the benzocoumarin formation is of interest, involving nickalocyclopentene and oxanickalocycle as key intermediates. A methodology for the synthesis of dibenzocoumarins has been discussed in chapter 2. The reaction of 7-oxabenzonorbornadienes with methyl 2-iodobenzoates in the presence of nickel catalyst gave dibenzocoumarins in moderate to good yields. The nickel-catalyzed one-pot reaction also affords highly conjugated dibenzocoumarins, albeit in moderate yields.
Nickel-catalyzed carbocyclization reaction is described in chapter 3. Various indenol derivatives have been synthesized from the reaction of ortho-iodophenyl ketones with alkyl propiolates catalyzed by nickel complexes. This carbocyclization reaction is highly regioselective providing indenols in moderate to excellent yields. The proposed mechanism involves vinyl-nickel as key intermediate.
A nickel-catalyzed cyclization reaction for the synthesis of medium-size ring lactones has been investigated in chapter 4. The reaction of 2-iodobenzyl alcohols with alkyl propiolates catalyzed by nickel complexes affords seven-member lactones in moderate to good yields with high regio and stereoselectivity. The important aspect of the mechanism is the Lewis-acid promoted cis-trans isomerization step.
Reductive coupling reaction of oxa- and azabicyclic alkenes with alkyl propiolates to give ring opening addition products catalyzed by nickel complexes has been described in chapter 5. The ring opening reaction affords 2-alkenyl-1,2-dihydroarenes derivatives with remarkable regio- and diastereoselectivity and under very mild conditions. In addition, the reductive coupling reaction is atom economical. The methodology is also applicable for the synthesis of functionalized cyclohexenols and bicyclic--lactones in good yields with excellent selectivity. Chapter 6 describes about the synthesis of 2-alkynyl-1,2-dihydroarenes derivatives from the reaction of oxa- and azabicyclic alkenes with terminal acetylenes in the presence of nickel complexes. The ring-opening addition reaction offers a convenient method for the construction of the dihydronaphthalene framework in one pot from easily accessible starting material. Significant feature of this nickel-catalyzed reaction is the mechanism. The active catalyst for the present reaction is Ni(II) unlike in other reactions, where Ni(0) was the active species.

page
ACKNOWLEDGEMENT iv ABSTRACT v
LIST OF SCHEMES vii
LIST OF TABLES xi
LIST OF PUBLICATIONS xiii
LIST OF ABBREVATIONS xv
CHAPTER 1: Nickel-Catalyzed Highly Regio- and
Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of
Benzocoumarin Derivatives 1
Introduction 2
Results and Discussion 14
Conclusion 34
Experimental Section 35
References 53
CHAPTER 2: Nickel-Catalyzed Cyclization of Oxanorbornenes
with o-Iodobenzoates: An Efficient Route to
Dibenzocoumarin Derivatives 58
Introduction 59
Results and Discussion 61
Conclusion 70
Experimental Section 71
References 77
CHAPTER 3: Nickel-Catalyzed Regioselective Carbocyclization
of ortho-Halophenyl Ketones with Propiolate: An Efficient
Route to Disubstituted Indenols 80
Introduction 81
Results and Discussion 92
Conclusion 104
Experimental Section 105
References 115
CHAPTER 4: Synthesis of Seven-Membered Lactones via Nickel-
and Zinc-Catalyzed Highly Regio- and Stereoselective Cyclization of 2-Iodobenzyl Alcohols with Propiolates 119
Introduction 120
Results and Discussion 132
Conclusion 147
Experimental Section 148
References 158
CHAPTER 5: Regio- and Stereoselective Reductive Coupling of Bicyclic Alkenes with Propiolates via Nickel Catalysis: An Efficient Route to Functionalized Cyclohexenols and 1,2-Dihydroarenes 161
Introduction 162
Results and Discussion 172
Conclusion 189
Experimental Section 190
References 205
CHAPTER 6: Highly Stereoselective Ring-Opening Addition of Terminal Acetylenes to Bicyclic Olefins Catalyzed by Nickel Complexes 209
Introduction 210
Results and Discussion 212
Conclusion 223
Experimental Section 224
References 235
CRYSTAL STRUCTURES AND 1H & 13C NMR SPECTRA 238

CHAPTER 1
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CHAPTER 2
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CHAPTER 3
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CHAPTER 4
(1) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
(2) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270
(3) Larock, R. C.; Doty. M. J.; Han, X. J. Org. Chem. 1999, 64, 8770 and references therein.
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(40) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
(41) For nickel oxametallacycles see (a) Kimura, M.; Matsuo, S.; Shibata, K.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 3386. (b) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891.
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CHAPTER 6
(1) (a) Huang, D. -J.; Sambaiah, T.; Cheng, C. -H. New J. Chem. 1998, 22, 1147. (b) Sambaiah, T.; Huang, D. -J.; Cheng, C. -H. J. Chem. Soc. Perkin. Trans 1. 2000, 195.
(2) For other nickel-catalyzed [2+2+2] cycloadditions from our lab see (a) Hsiao, T. -Y.; Santhosh, K. C.; Liou, K. -F.; Cheng, C. -H. J. Am. Chem. Soc. 1998, 120, 12232. (b) Sambaiah, T.; Li, L. -P.; Huang, D. -J.; Lin, C. -H.; Rayabarapu, D. K.; Cheng, C. -H. J. Org. Chem. 1999, 64, 3663. (c) Shanmugasundaram, M.; Wu, M. -S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233.
(3) Huang, D. -J.; Rayabarapu, D. K.; Li, L. -P.; Sambaiah, T.; Cheng, C. -H., Chem. Eur. J. 2000, 6, 3706.
(4) Rayabarapu, D. K.; Sambaiah, T.; Cheng, C. -H. Angew. Chem. Int. Ed. Engl. 2001, 40, 1286.
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(8) (a) Murakami, M.; Igawa, H. J. Chem. Soc., Chem. Commun. 2002, 390. (b) Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067. (c) Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259.
(9) (a) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804. (b) Lautens, M.; Fagnou, K.; Rovis, T. J. Am. Chem. Soc. 2000, 122, 5650. (c) Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 12, 1677. d) Lautens, M.; Hiebert, S.; Renaud, J.-L. Org. Lett. 2000, 13, 1971.
(10) (a) Lautens, M.; Rovis, T. J. Am. Chem. Soc. 1997, 119, 11090. (b) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532. (c) Lautens, M.; Ma, S. J. Org. Chem. 1996, 61, 7246. (d) Lautens, M. Rovis, T. J. Org. Chem. 1997, 62, 5246.
(11) (a) Lautens, M. Pure Appl. Chem. 1992, 64, 1873. (b) Lautens, M.; Ma, S. Tetrahedron Lett. 1996, 37, 1727. (c) Woo, S.; Keay, B. A. Synthesis 1996, 669. (d) Arjona, O.; Conde, S.; Plumet, J.; Viso, A. Tetrahedron Lett. 1995, 36, 6157. (e) Lautens, M.; Fillon, E.; Sampat, M. J. Org. Chem. 1997, 62, 7080. (f) Gillespie, D. G.; Wlaker, B. J.; Stevens, D.; McAuliffe, C. A.; J. Chem. Soc., Perkin Trans. 1. 1983, 1697. (g) Cuny, G. D.; Buchwald, S. L. Organometallics 1991, 10, 363. (h) Moinet, C.; Fiaud, J. C. Tetrahedron Lett. 1995, 36, 2051. (i) Fugami, K.; Hagiwara, S.; Oda, H.; Kosugi, M. Synlett. 1998, 477. (j) Lautens, M.; Klute, W. Angew. Chem. Int. Ed. Engl. 1996, 35, 442.
(12) (a) Johnson, B. M.; Chang, P. T. L. Analytical Profiles of Drug Substances and Excipients 1996, 24, 443. (b) Synder, S. E. J. Med. Chem. 1995, 38, 2395. (c) Kamal, A.; Gayatri, L.; Tetrahedron Lett. 1996, 37, 3359. (d) Kim, K.; Guo, Y.; Sulikowski, G. A. J. Org. Chem. 1995, 60, 6866. (e) Perrone, R. J. Med. Chem. 1995, 38, 942.
(13) (a) Duan, J. P.; Cheng, C. H. Tetrahedron Lett. 1993, 34, 4019. (b) Duan, J. P.; Cheng, C. H. Organometallics 1995, 14, 1608.
(14) Feng, C. C.; Nandi, M.; Sambaiah, T.; Cheng, C. H. J. Org. Chem. 1999, 64, 3538.
(15) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687 and references therein.
(16) For mechanistic studies see; Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2001, 123, 6834.
(17) (a) Kende, A. S.; Liebeskind, L. S.; Braitsen, D. M. Tetrahedron Lett. 1975, 3375. (b) Zembayashi, M.; Tamao, K.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 4089