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Ag-Catalyzed Asymmetric Mannich Reactions of Enol Ethers with Aryl, Alkyl, Alkenyl, and Alkynyl Imines

Nathan S. Josephsohn, Marc L. Snapper and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: amir.hoveydabc.edu

N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc., 2004, 126, 3734-3735.

DOI: 10.1021/ja049388e (free Supporting Information)


Abstract

An efficient catalytic and enantioselective method for Mannich reactions between trimethylsilyl enol ethers derived from acetone and acetophenone and aryl, alkenyl, alkynyl, and alkyl imines allows the synthesis of a various β-amino ketones in the presence of 1-5 mol % AgOAc and an inexpensive amino acid-derived phosphine.

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Key Words

Mannich reaction, β-amino ketones, multicomponent reactions


ID: J48-Y2004-1450