Lewis Base-Catalyzed [2, 3]-Wittig Rearrangement of Silyl Enolates Generated from. ALPHA.-Allyloxy Carbonyl Compounds

Y Sato, H Fujisawa, T Mukaiyama

Index: Sato, Yoshinori; Fujisawa, Hidehiko; Mukaiyama, Teruaki Bulletin of the Chemical Society of Japan, 2006 , vol. 79, # 8 p. 1275 - 1287

Full Text: HTML

Citation Number: 8

Abstract

Lewis base-catalyzed [2, 3]-Wittig rearrangement of silyl enolates generated from α-allyloxy carbonyl compounds is described. The [2, 3]-Wittig rearrangement of silyl enolates generated from α-allyloxy ketones proceeded smoothly by using a Lewis base catalyst, such as lithio or sodio 2-pyrrolidone, in DMF at room temperature without an accompanying [3, 3]- Claisen rearrangement. The nature of the catalyst determines the pathway to proceed ...