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Asymmetric Morita-Baylis-Hillman Reactions Catalyzed by Chiral Brønsted Acids

Nolan T. McDougal and Scott E. Schaus*

*Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, Email: seschauschem.bu.edu

N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc., 2003, 125, 12094-12095.

DOI: 10.1021/ja037705w (free Supporting Information)


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Abstract

Chiral BINOL-derived Brønsted acids catalyze a highly enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The reaction requires 2-20 mol% of the chiral Brønsted acid and triethylphosphine as the nucleophilic promoter.

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Key Words

Baylis-Hillman reaction, Cyclohexenones


ID: J48-Y2003-1600