Direct, Stereospecific Generation of (Z)-Disubstituted Allylic Alcohols

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• 作者：Sang-Jin Jeon ; Ethan L. Fisher ; Patrick J. Carroll ; Patrick J. Walsh
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：August 2, 2006
• 年：2006
• 卷：128
• 期：30
• 页码：9618 - 9619
• 全文大小：59K
• 年卷期：v.128,no.30(August 2, 2006)
• ISSN：1520-5126

文摘

A one-pot method to prepare highly functionalized (Z)-disubstituted allylic alcohols is introduced. Hydroboration of a variety of 1-bromo-1-acetylenes with dicyclohexyl borane, reaction with t-BuLi, and transmetalation to zinc generates a (Z)-disubstituted vinylzinc reagent. In situ reaction of this reagent with aldehydes generates (Z)-disubstituted allylic alcohols in high yields (81-97%). Addition to chiral protected - or -oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases.