A new 1,1'-binaphthyl-based catalyst for the enantioselective phenylacetylene addition to aromatic aldehydes without using a titanium complex

Ming-Hua Xu; Lin Pu

doi:10.1021/ol027110q

A new 1,1'-binaphthyl-based catalyst for the enantioselective phenylacetylene addition to aromatic aldehydes without using a titanium complex

Org Lett. 2002 Dec 12;4(25):4555-7. doi: 10.1021/ol027110q.

Authors

Ming-Hua Xu¹, Lin Pu

Affiliation

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

PMID: 12465936
DOI: 10.1021/ol027110q

Abstract

[reaction: see text] A novel 1,1'-binaphthyl compound containing bulky 3,3'-aryl substituents is found to catalyze the reaction of a terminal alkyne with various aromatic aldehydes under mild conditions to generate chiral propargyl alcohols with 80-94% ee. Unlike the previously reported 1,1'-binaphthyl catalysts, this new compound does not require the use of a titanium complex and the pre-preparation of an alkynylzinc. This has greatly simplified the experimental procedure for this reaction.