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. 2004 Apr 13;101(15):5417-20.
doi: 10.1073/pnas.0307136101. Epub 2004 Mar 16.

Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide

Ge Gao  1 , Ru-Gang Xie, Lin Pu
Affiliations

Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide

Ge Gao et al. Proc Natl Acad Sci U S A. .

Abstract

It is found that the addition of hexamethylphosphoramide to the solution of an alkyne, Et(2)Zn, and (S)-1,1'-bi-2-naphthol in methylene chloride allows the generation of an alkynylzinc at room temperature and shows highly enantioselective additions to aldehydes. The mild condition for the formation of the alkynylzinc reagent enables the use of functional alkynes in this asymmetric reaction with excellent enantioselectivity. It avoids the reflux of the toluene solutions of the alkynes and Et(2)Zn as previously reported.

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Figures

Scheme 1.
Scheme 1.
Scheme 2.
Scheme 2.
The asymmetric reaction of phenylacetylene with benzaldehyde.
See this image and copyright information in PMC

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