Menthyl 2-bromocrotonate and menthyl 4-bromocrotonate: reagents for chiral vinylogous Darzens and Reformatsky reactions

T Hudlicky, L Radesca, HL Rigby

Index: Hudlicky, Tomas; Radesca, Lilian; Rigby, H. Lee Journal of Organic Chemistry, 1987 , vol. 52, # 19 p. 4397 - 4399

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Citation Number: 15

Abstract

" Reagents:(a) menthol (both d and 1 isomers), Et3N;(b) DBU, THF;(c) Br,. CC1,;(d) DBU, DME. the regioselective vinylogous Reformatsky rea~ tion,~ respectively. The use of menthyl esters 1 and 2 in identical sequences was shown to have a good chiral auxiliary effect and the above reactions produced chiral vinylcyclopropanes4 or chiral 1, 3-di0ls,~ respectively. The preparation of both halo esters in the 1 series commenced with the condensation of ...