Direct, stereospecific generation of (Z)-disubstituted allylic alcohols

Sang-Jin Jeon; Ethan L Fisher; Patrick J Carroll; Patrick J Walsh

doi:10.1021/ja061973n

Direct, stereospecific generation of (Z)-disubstituted allylic alcohols

J Am Chem Soc. 2006 Aug 2;128(30):9618-9. doi: 10.1021/ja061973n.

Authors

Sang-Jin Jeon¹, Ethan L Fisher, Patrick J Carroll, Patrick J Walsh

Affiliation

¹ P. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

PMID: 16866501
DOI: 10.1021/ja061973n

Abstract

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 alpha- or beta-oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Catalysis
Molecular Structure
Propanols / chemical synthesis*

Substances

Propanols
allyl alcohol

Grants and funding

GM58101/GM/NIGMS NIH HHS/United States