Chiral phosphoric acid-catalyzed oxidative kinetic resolution of indolines based on transfer hydrogenation to imines

Kodai Saito; Yukihiro Shibata; Masahiro Yamanaka; Takahiko Akiyama

doi:10.1021/ja406004q

Chiral phosphoric acid-catalyzed oxidative kinetic resolution of indolines based on transfer hydrogenation to imines

J Am Chem Soc. 2013 Aug 14;135(32):11740-3. doi: 10.1021/ja406004q. Epub 2013 Jul 25.

Authors

Kodai Saito¹, Yukihiro Shibata, Masahiro Yamanaka, Takahiko Akiyama

Affiliation

¹ Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.

PMID: 23865933
DOI: 10.1021/ja406004q

Abstract

The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrogenation
Imines / chemistry*
Indoles / chemistry*
Kinetics
Oxidation-Reduction
Phosphoric Acids / chemistry*
Stereoisomerism

Substances

Imines
Indoles
Phosphoric Acids
indoline
phosphoric acid