TY - JOUR AU - Katayev, Dmitry AU - Nakanishi, Masafumi AU - Bürgi, Thomas AU - Kündig, E.Peter TI - Asymmetric C(sp3)-H/C(Ar) coupling reactions. Highly enantio-enriched indolines via regiodivergent reaction of a racemic mixture PY - 2012 JF - Chemical Science JA - Chem. Sci. SN - 2041-6520 VL - 3 IS - 5 SP - 1422 EP - 1425 L1 - http://pubs.rsc.org/en/content/articlepdf/2012/sc/c2sc20111a L2 - http://pubs.rsc.org/en/content/articlehtml/2012/sc/c2sc20111a L3 - http://xlink.rsc.org/?DOI=c2sc20111a M3 - 10.1039/c2sc20111a UR - http://dx.doi.org/10.1039/c2sc20111a N2 - 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. ID - 1292 ER -