. alpha.-Silyl aldehydes: preparation and use as stereoselective vinyl cation equivalents

PF Hudrlik, AK Kulkarni

Index: Hudrlik, Paul F.; Kulkarni, Ashok K. Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6251 - 6253

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Citation Number: 88

Abstract

(72-79% yields) 94% cis 97% cis 99% cis a (a) BF,. Et, O, CHzClZ, room temperature, 1 h.@) KH, THF, room temperature, 2 h. and Kuwajima'* have shown that a-trimethylsilyl aldehydes can be generated and trapped in situ by Grignard reagents. We now report a potentially general method for preparing a-tert-butyldimethylsilyl aldehydes by hydrolysis of the corresponding a-silyl imines and the use of these aldehydes as vinyl cation equivalents. ...