(E)-and (Z)-1-(Phenylsulfonyl)-4-(trimethylsilyl)-2-butenes: Synthetic Equivalents for the 1-(1, 3-Butadienyl) Anion and the 1, 1-(1, 3-Butadienyl) Dianion

TP Meagher, L Yet, CN Hsiao…

Index: Meagher, Timothy P.; Yet, Larry; Hsiao, Chi-Nung; Shechter, Harold Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4181 - 4192

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Citation Number: 17

Abstract

(E)-and (Z)-1-(phenylsulfonyl)-4-(trimethylsilyl)-2-butenes (7 and 8) are converted by n-BuLi to (E)-and (Z)-1-lithio-1-(phenylsulfonyl)-4-(trimethylsilyl)-2-butenes (15 and 16) with retention of initial stereochemistries. Reactions of 15 and 16 with electrophiles (protio and deuterio acids, primary, secondary, and benzyl halides, chloroformates, chlorothioformates, acid chlorides, epoxides, trialkylsilyl chlorides, and triethylgermanyl chloride) in THF or ...