The Journal of Organic Chemistry

Metalation reactions of 1-silacyclo-3-pentenes

RF Horvath, TH Chan

Index: Horvath, R. F.; Chan, T. H. Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4489 - 4494

Full Text: HTML

Citation Number: 21

Abstract

6a 6b of interest is the regioselectivity of the reaction of 2 with electrophiles. The a-silylallyl anion is known to react with electrophiles with y-selectivity, giving stereoselectively the (E)- vinylsilane 3.3 This is presumably due to the transoid stereochemistry of 4. Because of the cyclopentyl structure, the anion 2 has to adopt a cisoid stereochemistry. This stereochemical change may modify the regioselection of the reaction of the anion with electrophiles ( ...