通过铑（I）催化烯基三氟硼酸盐加成到N-叔丁基亚磺酰亚胺上不对称合成α-支链烯丙基胺。

Asymmetric synthesis of alpha-branched allylic amines by the Rh(I)-catalyzed addition of alkenyltrifluoroborates to N-tert-butanesulfinyl aldimines.

作者信息

Brak Katrien, Ellman Jonathan A

机构信息

Department of Chemistry, University of California, Berkeley, California 94720, USA.

出版信息

J Am Chem Soc. 2009 Mar 25;131(11):3850-1. doi: 10.1021/ja9002603.

DOI:10.1021/ja9002603

PMID:19256498

Abstract

The first Rh(I)-catalyzed addition of alkenylboron reagents to imines is described. The Rh(I)-catalyzed addition of potassium alkenyltrifluoroborate salts to both aromatic and aliphatic N-tert-butanesulfinyl aldimines proceeds in good yields (up to 97%) and with very high diastereoselectivities (95:5 to >99:1). This new method enables the general and efficient asymmetric synthesis of the important class of alpha-branched allylic amines from readily available and stable starting materials.

摘要

首次报道了铑（I）催化的烯基硼试剂与亚胺的加成反应。铑（I）催化的烯基三氟硼酸钾盐与芳香族和脂肪族N-叔丁基亚磺酰醛亚胺的加成反应产率良好（高达97%），非对映选择性极高（95:5至>99:1）。这种新方法能够从容易获得且稳定的起始原料出发，实现重要的α-支链烯丙基胺类化合物的通用且高效的不对称合成。