通过吲哚的催化不对称氢化反应高度对映选择性合成手性3-取代吲哚啉。

Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles.

作者信息

Kuwano Ryoichi, Kaneda Kohei, Ito Takashi, Sato Koji, Kurokawa Takashi, Ito Yoshihiko

机构信息

Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.

出版信息

Org Lett. 2004 Jun 24;6(13):2213-5. doi: 10.1021/ol049317k.

DOI:10.1021/ol049317k

PMID:15200323

Abstract

[reaction: see text] N-Tosyl 3-substituted indoles were hydrogenated with high enantioselectivities (95-98% ee) by use of a trans-chelating chiral bisphosphine, (S,S)-(R,R)-PhTRAP ligand. The chiral catalyst, which was generated in situ from [Rh(nbd)(2)]SbF(6), PhTRAP, and Cs(2)CO(3), is useful for enantioselectively synthesizing a range of diverse optically active indolines possessing a chiral carbon at the 3-position.

摘要

[反应：见正文] 通过使用反式螯合手性双膦（S,S）-（R,R）-PhTRAP配体，N-对甲苯磺酰基-3-取代吲哚以高对映选择性（95-98% ee）进行氢化反应。由[Rh（nbd）₂]SbF₆、PhTRAP和Cs₂CO₃原位生成的手性催化剂，可用于对映选择性合成一系列在3-位具有手性碳的多种不同光学活性吲哚啉。