Guanidines in organic synthesis

被引：231

作者：

Ishikawa, T ^{[1
]}

Kumamoto, T ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chiba 2638522, Japan

来源：

SYNTHESIS-STUTTGART | 2006年 / 05期

关键词：

catalysis; asymmetric synthesis; chiral auxiliary; guanidine; organic base;

D O I：

10.1055/s-2006-926325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Guanidine is categorized as an organic superbase, yet its synthetic application is immature despite its wide potential utility. The role of guanidine in organic synthesis, including asymmetric reactions, is discussed herein. 1 Introduction 2 TMG and Its Analogues in Organic Synthesis 2.1 Alkylation of Carboxylic Acids 2.2 Barton's Bases 2.3 Baylis-Hillman Reactions 2.4 Bismuth-Mediated Reactions 2.5 Cyclopropanations 2.6 Horner-Emmons Reactions 2.7 Ionic Liquids 2.8 Michael Reactions 2.9 Nitroaldol (Henry) Reactions 2.10 Nucleophilic Reactions with Thiols 2.11 Palladium-Catalyzed Reactions 2.12 Silylation of Alcohols 2.13 Supported Guanidines 2.14 TMG Azides 3 Applications toward Asymmetric Synthesis 3.1 Alkylation of Carboxylic Acids 3.2 Alkylation of Schiff Bases 3.3 Azidations 3.4 Michael Reactions 3.5 Nitroaldol (Henry) Reactions 3.6 Nucleophilic Epoxidations 3.7 Silylation of Alcohols 3.8 Strecker Reactions 3.9 TMS Cyanations 3.10 Others 4 Conclusion.

引用

页码：737 / 752

页数：16

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