The Journal of organic chemistry

Benzotriazole-mediated [2, 3]-Wittig rearrangement. General and Stereocontrolled syntheses of homoallyl alcohols and β, γ-unsaturated ketones

AR Katritzky, H Wu, L Xie

Index: Katritzky, Alan R.; Wu, Hong; Xie, Linghong Journal of Organic Chemistry, 1996 , vol. 61, # 12 p. 4035 - 4039

Full Text: HTML

Citation Number: 18

Abstract

Readily accessible allyl 1-(benzotriazol-1-yl) alkyl ethers (13 and 19), upon treatment with 2.5 equiv of nucleophilic lithium reagents, give secondary and tertiary homoallyl alcohols (16 and 21), respectively, exclusively in the E configuration in excellent yields. This is achieved by deprotonation followed by [2, 3]-Wittig rearrangement, departure of the benzotriazolyl group, and then nucleophilic addition to the resulting carbonyl compound. ...