Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization

被引:61
作者
Lam, HW [1 ]
Murray, GJ [1 ]
Firth, JD [1 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
关键词
D O I
10.1021/ol052599j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Hydroxypiperidin-2-ories 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.
引用
收藏
页码:5743 / 5746
页数:4
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