Synfacts 2007(1): 0091-0091  
DOI: 10.1055/s-2006-955662
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Nonenzymatic Kinetic Resolution of Indolines

Contributor(s): Benjamin List, Sebastian Hoffmann
F. O. Arp, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
15 December 2006 (online)

Significance

The first kinetic resolution of 2-substituted indolines 1 through catalytic N-acylation is described. The planar chiral pyridine derivative 4 functions as a Lewis basic catalyst, leading to the resolved indolines 2 in very good enantioselectivities (up to er = 99:1) after 51-65% conversion. Notably, 2,3-disubstituted indolines are also suitable substrates and substituents in the 5-position are tolerated.