N-亚磺酰基金属烯胺共轭加成：哌啶的不对称合成

N-sulfinyl metalloenamine conjugate additions: asymmetric synthesis of piperidines.

作者信息

Peltier Hillary M, Ellman Jonathan A

机构信息

Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.

出版信息

J Org Chem. 2005 Sep 2;70(18):7342-5. doi: 10.1021/jo051020s.

DOI:10.1021/jo051020s

PMID:16122257

Abstract

[reaction: see text] The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.

摘要

[反应：见正文] 报道了N-叔丁基亚磺酰基金属烯胺共轭加成的首例。观察到由N-亚磺酰基酮亚胺衍生的金属烯胺与带有烷基或芳基取代基的α,β-不饱和酮之间发生了高度立体选择性的共轭加成（非对映体比例为97:3至99:1）。共轭加成产物可以以高非对映选择性快速转化为2,4,6-三取代哌啶，而通过其他方法难以得到这些产物。