Asymmetric C(sp(3))-H/C(Ar) coupling reactions. Highly enantio-enriched indolines via regiodivergent reaction of a racemic mixture

作者:Katayev Dmitry; Nakanishi Masafumi; Buergi Thomas; Kuendig E Peter
来源:Chemical Science, 2012, 3(5): 1422-1425.
DOI:10.1039/c2sc20111a

摘要

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.

  • 出版日期2012