Organic letters

Syntheses with organoboranes. XI. Allylboration Of vinylic epoxides with allylic dialkylboranes

M Zaidlewicz, MP Krzeminski

Index: Zaidlewicz, Marek; Krzeminski, Marek P. Organic Letters, 2000 , vol. 2, # 24 p. 3897 - 3899

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Citation Number: 4

Abstract

Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2- cyclohexenyl) dicyclohexylborane (2) affords the corresponding 1, 2-and 1, 4-addition products. cis-1, 2-Addition is favored in the reaction of 1 with 3, 4-epoxycycloalkenes of six- to eight-membered rings. 3, 4-Epoxycyclopentene (3a) and 5, 5-dimethyl-3, 4- epoxycyclopentene (3b) undergo five-membered ring opening during allylboration with 1 ...