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Facile, Mild, and Highly Enantioselective Alkynylzinc Addition to Aromatic Aldehydes by BINOL/N-Methylimidazole Dual Catalysis

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journal contribution
posted on 06.07.2007, 00:00 by Fei Yang, Peihua Xi, Li Yang, Jingbo Lan, Rugang Xie, Jingsong You
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.