67826-82-8Relevant academic research and scientific papers
Direct, stereospecific generation of (Z)-disubstituted allylic alcohols
Jeon, Sang-Jin,Fisher, Ethan L.,Carroll, Patrick J.,Walsh, Patrick J.
, p. 9618 - 9619 (2007/10/03)
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 α- or β-oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases. Copyright
