一种通过金催化合成哌啶-4-酮的两步、形式上的[4 + 2]方法。

A two-step, formal [4 + 2] approach toward piperidin-4-ones via Au catalysis.

作者信息

Cui Li, Peng Yu, Zhang Liming

机构信息

Department of Chemistry/216, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, USA.

出版信息

J Am Chem Soc. 2009 Jun 24;131(24):8394-5. doi: 10.1021/ja903531g.

DOI:10.1021/ja903531g

PMID:19492799

Abstract

An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstrated in a highly diastereoselective synthesis of (+/-)-cermizine C.

摘要

通过关键的金催化作用，在两步反应中从仲胺高效、形式上实现了合成有价值的哌啶-4-酮的[4 + 2]合成，无需纯化叔胺中间体。该反应对取代较少的烷基具有选择性，并显示出中等至优异的非对映选择性。其在生物碱合成中的合成潜力在(+/-)-塞米嗪C的高度非对映选择性合成中得到了证明。