Organic syntheses using indium-mediated and catalyzed reactions in aqueous media

Abstract

I. Introduction 11. Indium Mediated Barbier-Type Reactions 2.1. The reaction 2.2. Mechanism of indium-mediated Barbier-type reactions 2.3. The regio- and stereochemistry of indium-mediated reactions 2.4. Synthetic applications of indium-mediated reactions 2.4.1. Synthesis of sialic acids and carbohydrate homologations 2.4.2. Styryl carbohydrates 2.4.3. 13-Lactams 2.4.4. Carbocycles 2.4.5. Other examples III. Transmetalation Reactions with Indium Metal or Indium Salts IV. Other Indium-Mediated Reactions V. Indium Salts as Water-Tolerant Lewis Catalysts 5.1. Barbier-type reactions 5.2. Mukaiyama-aldol reactions 5.3. Other reactions VI. Conclusions 11149 11150 11150 11153 11154 11160 11160 11164 11165 11165 11167 11167 11168 11170 11170 11170 11171 11172 1. Introduction While the development of boron and aluminum reagents for synthetic purposes has been one of the major achievements in organic chemistry in this century, the study of indium reagents has remained largely unexplored until very recently.t The earliest study of using indium for synthetic purposes was carried out briefly earlier this century.2 In the 1970s, Rieke developed various active metals (including indium), now commonly referred to as 0040-4020/99/$ - see front matter © 1999 Elsevier Science Ltd. All rights reserved. PH: S0040-4020(99)00641-9