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Diastereoselective Synthesis of 4-Hydroxypiperidin-2-ones via Cu(I)-Catalyzed Reductive Aldol Cyclization

2005; American Chemical Society; Volume: 7; Issue: 25 Linguagem: Inglês

10.1021/ol052599j

1523-7060

Hon Wai Lam, Gordon J. Murray, James D. Firth,

Chemical synthesis and alkaloids

[chemical reaction: see text]. 4-Hydroxypiperidin-2-ones may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of alpha,beta-unsaturated amides with ketones. Used in combination with proline-catalyzed asymmetric Mannich reactions, this methodology enables the enantioselective synthesis of more highly functionalized piperidin-2-ones and hydroxylated piperidines.