Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes

Ge Gao; David Moore; Ru-Gang Xie; Lin Pu

doi:10.1021/ol026921r

Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes

Org Lett. 2002 Nov 14;4(23):4143-6. doi: 10.1021/ol026921r.

Authors

Ge Gao¹, David Moore, Ru-Gang Xie, Lin Pu

Affiliation

¹ Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.

PMID: 12423107
DOI: 10.1021/ol026921r

Abstract

The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction. [reaction: see text]

Publication types

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

MeSH terms

Acetylene / analogs & derivatives*
Acetylene / chemistry*
Aldehydes / chemical synthesis*
Aldehydes / chemistry*
Indicators and Reagents
Models, Molecular
Molecular Conformation
Stereoisomerism

Substances

Aldehydes
Indicators and Reagents
phenylacetylene
Acetylene

Grants and funding

R01 GM 58454/GM/NIGMS NIH HHS/United States