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研究生:沙強生
研究生(外文):Reniguntala Johnson Madhu Shaw
論文名稱:金屬鎢、釕應用於含氧、氮雜環化合物之環化反應
論文名稱(外文):Syntheses of Oxygen and Nitrogen Heterocycles Using Tungsten and Ruthenium Mediated Cyclizations
指導教授:劉瑞雄
指導教授(外文):Prof. Rai-Shung Liu
學位類別:博士
校院名稱:國立清華大學
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
論文出版年:2002
畢業學年度:90
語文別:英文
論文頁數:326
中文關鍵詞:鎢環化反應釕環化反應
外文關鍵詞:Tungsten CyclizationsRuthenium Cyclizations
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  • 點閱點閱:100
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  • 收藏至我的研究室書目清單書目收藏:1
詳見英文摘要
The thesis discusses several new tungsten and ruthenium mediated cycloaddition reactions and their application in organic synthesis. For convenience and better understanding, the thesis is divided in to three chapters. The first two chapters deals with tungsten mediated cycloaddition reactions and the third chapter deals with ruthenium mediated cycloaddition reactions and application in organic synthesis.
The synthesis of organic carbocyclic and heterocyclic systems from acyclic building blocks is typically achieved through the use of either condensation or cycloaddition process. The reactions of Co2(CO)8 with alkynes RCCR¢ form (RCCR¢)-Co2(CO)6 complexes. The versatility of these reactions is well recognized, and they are frequently employed as a key step in synthesis of complex molecules. Development of new synthetic method involving carbenoid intermediates has received considerable attention. Although there are numerous investigations on (RC≡CR¢)Co2(CO)6 complexes, generation of a carbenoid intermediate from this functionality remains entirely unknown. In chapter-I we describe several intramolecular cyclizations via carbenoid intermediates generated from Co2(CO)6 complexation of funtionalized alkynyltungsten compounds. The synthetic utility of these cyclizations is manifested in the synthesis of cyclopentenone derivatives.
The cycloaddition of alkynes and alkenes with organic substrate is widely used for the synthesis of carbocyclic and heterocyclic compounds. Epoxides and aziridines are important substances, and the cycloaddition of these molecules with alkenes alkynes is an interesting topic in organic synthesis. In chapter-II we report two useful cyclizations based on alkynyltungsten compounds, and each reaction involves sequential bond-breaking and —forming process. [3+2]-Cycloaddition of epoxides and aziridines with alkynes are hitherto unreported to the best of our knowledge. In this study, we describe a new cycloaddition of common epoxides and trans-aziridines with funtionalized alkynes. These methods are applicable to the enantiocontrolled synthesis of complex bicyclic lactones and lactams. Significant feature of this cycloaddition is that, it provides a one pot synthesis of bicyclic lactones via a tungsten enol ether.
In chapter-III we describe the syntheses of various chiral oxacyclic dienes via enyne metathesis using Grubbs Catalyst (PCy3)2Cl2Ru=CHPh. These oxacyclic dienes are designed to bear a (2S)-(alkoxy)ethyl group derived from natural (2S)-ethyl lactate. The role of this substituent is twofold in synthetic application (1) control of diastereoselective Diels-Alder reaction (2) easy degradation into a common functionality after cycloadditon reaction. Our present approach for the synthesis of chiral oxacyclic dienes was extended for the construction of enantiopure tricyclic furan derivatives.
Fused bicyclic [n.m.0] structural frameworks represent an important substructure in many natural products, and development of new synthetic approaches to these skeletons continues to be an important goal. Our enyne metathesis approach toward the synthesis of chiral oxacyclic dienes led us to focus on the construction of functionalized chiral oxabicyclic products that contain five-, six- and seven-membered rings by tandem RCM of dienynes using Grubbs ruthenium catalyst. Using this Tandem RCM approach variety of chiral fused bicyclic [n.m.0] rings can be constructed from simple precursors.
TABLE OF CONTENTS
Page
ACKNOWLEDGEMENT iii
ABSTRACT v
LIST OF SCHEMES vii
LIST OF TABLES xii
LIST OF FIGURES xiii
LIST OF PUBLICATIONS xiv
ABBREVIATIONS xv
CHAPTER I: Intramolecular Cyclizations via Carbenoid Intermediates in Complexation of Alkynyltungsten Compounds with Co2(CO)8: A new Route to the Pauson-Khand Reaction.
Introduction 1
Results and Discussion 14
Conclusion 32
CHAPTER II: Tungsten-Promoted [3+2]-Cycloaddition of Epoxides and
Aziridines with Alkynes. A Facile Enantiospecific Synthesis of Bicyclic
Lactones.
Introduction 33
Results and Discussion 44
Conclusion 65
CHAPTER III: Synthesis of Chiral Oxacyclic Dienes via Ruthenium-Cataly-
-zed Enyne Metathesis: Useful Building Blocks for Chiral Tricyclic Oxy-
-gen Derivatives.
Introduction 66
Results and Discussion 75
Conclusion 86
Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic
rings.
Introduction 87
Results and Discussion 90
Conclusion 97
EXPERIMENTAL SECTION 98
REFERENCES 184
CRYSTAL STRUCTURES, 1H AND 13C NMR SPECTRA 194
1H-1H AND 1H-13C COSY SPECTRA 320
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