Issue 5, 2012

Asymmetric C(sp3)-H/C(Ar) coupling reactions. Highly enantio-enriched indolines via regiodivergent reaction of a racemic mixture

Abstract

N-Aryl, N-branched alkyl carbamates react with in situ generated chiral Pd-NHC catalysts by coupling a Pd-Ar moiety with an aliphatic C–H bond at high temperature to give enantioenriched 2-substituted and 2,3-disubstituted indolines. Prochiral precursors give single products with very high asymmetric induction. Chiral racemic precursors react in a regiodivergent reaction of a racemic mixture to yield enantioenriched indolines resulting from either methyl C–H activation or asymmetric methylene C–H activation. In favorable cases this can result in a complete separation of an enatiomeric mixture into two different highly enantioenriched indolines.

Graphical abstract: Asymmetric C(sp3)-H/C(Ar) coupling reactions. Highly enantio-enriched indolines via regiodivergent reaction of a racemic mixture

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Jan 2012
Accepted
21 Feb 2012
First published
22 Feb 2012

Chem. Sci., 2012,3, 1422-1425

Asymmetric C(sp3)-H/C(Ar) coupling reactions. Highly enantio-enriched indolines via regiodivergent reaction of a racemic mixture

D. Katayev, M. Nakanishi, T. Bürgi and E. P. Kündig, Chem. Sci., 2012, 3, 1422 DOI: 10.1039/C2SC20111A

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