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

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

4-Hydroxypiperidin-2-ones may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of α,β-unsaturated amides with ketones. Used in combination with proline-catalyzed asymmetric Mannich reactions, this methodology enables the enantioselective synthesis...

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Veröffentlicht in:Organic letters 2005-12, Vol.7 (25), p.5743-5746
Hauptverfasser: Lam, Hon Wai, Murray, Gordon J, Firth, James D
Format: Artikel
Sprache:eng
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Zusammenfassung:4-Hydroxypiperidin-2-ones may be prepared in highly diastereoselective fashion using a Cu(I)-catalyzed reductive aldol cyclization of α,β-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052599j