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

J Org Chem

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China.

Published: July 2007

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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http://dx.doi.org/10.1021/jo0707535DOI Listing

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