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. 2007 Jul 6;72(14):5457-60.
doi: 10.1021/jo0707535. Epub 2007 Jun 8.

Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis

Fei Yang  1 , Peihua Xi, Li Yang, Jingbo Lan, Rugang Xie, Jingsong You
Affiliations

Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis

Fei Yang et al. J Org Chem. .

Abstract

The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1'-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the presence of Et2Zn in good yields and excellent enantioselectivities of up to 94% ee at room temperature. The mild reaction conditions make it possible to use functional alkynes in this asymmetric addition.

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