Triisobutylaluminium promoted reductive rearrangement of substituted vinyl ethers to homologous alcohols

B du Roizel, M Sollogoub, AJ Pearce…

Index: Du Roizel; Sollogoub; Pearce; Sinay Chemical Communications, 2000 , # 16 p. 1507 - 1508

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Citation Number: 5

Abstract

Lewis acid promoted oxygen to carbon rearrangements of vinyl acetals have received considerable attention as synthetically useful procedures. 1 For example, we have developed efficient methodology for the preparation of carbocycles by the reductive rearrangement of carbohydrate based vinyl acetals using TIBAL (triisobutylaluminium) as the Lewis acid. 2 We recently reported 3 that unsaturated C-aryl glycosides (hex-5-enopyranosides) such as 1, also undergo the analogous TIBAL ...