The Journal of Organic Chemistry

Regiospecific synthesis of homoallylic alcohols from tosylhydrazones

MF Lipton, RH Shapiro

Index: Lipton,M.F.; Shapiro,R.H. Journal of Organic Chemistry, 1978 , vol. 43, # 7 p. 1409 - 1413

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Citation Number: 33

Abstract

Regiospecifically generated tosylhydrazone dianions are trapped with aldehydes and ketones yielding i; l-hydrox-ytosylhydrazone dianions. Neutralization affords 6- hydroxytosylhydrazones, which may be converted with or without isolation cleanly and in good yield to homoallylic alcohols upon treatment with alkyllithium reagents. A ra-tionale is provided for the regiochemistry of this elimination. All attempts to obtain@-hydroxy ...