BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes

David Moore; Lin Pu

doi:10.1021/ol025825n

BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes

Org Lett. 2002 May 30;4(11):1855-7. doi: 10.1021/ol025825n.

Authors

David Moore¹, Lin Pu

Affiliation

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

PMID: 12027631
DOI: 10.1021/ol025825n

Abstract

[reaction: see text] The readily available BINOL ligand in combination with Ti(O(i)Pr)(4) was found to catalyze the highly enantioselective reaction (92-98% ee) of terminal alkynes with aromatic aldehydes that contain a variety of substituents and substitution patterns. After the preparation of the zinc acetylide reagent, the catalytic asymmetric addition to aldehydes proceeded at room temperature with excellent stereocontrol. This simple catalyst system is practical for the asymmetric synthesis of chiral propargylic alcohols.

Publication types

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

MeSH terms

Azetidines / chemical synthesis*
Catalysis
Freeze Drying
Hydroxylation
Piperidines / chemical synthesis*
Sphingomonas / metabolism*
Stereoisomerism

Substances

Azetidines
Piperidines