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. 2003 Oct 8;125(40):12094-5.
doi: 10.1021/ja037705w.

Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids

Nolan T McDougal  1 , Scott E Schaus
Affiliations

Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids

Nolan T McDougal et al. J Am Chem Soc. .

Abstract

Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39-88%) and high enantioselectivities (67-96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.

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