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

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

doi:10.1021/ol049317k

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

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

Authors

Ryoichi Kuwano¹, Kohei Kaneda, Takashi Ito, Koji Sato, Takashi Kurokawa, Yoshihiko Ito

Affiliation

¹ Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan. rkuwascc@mbox.nc.kyushu-u.ac.jp

PMID: 15200323
DOI: 10.1021/ol049317k

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.