American Chemical Society
jo2004204_si_001.cif (15.12 kB)

Asymmetric Synthesis of Benzylic Quaternary Difunctionalized Carbons Mediated by a Remote Sulfinyl Group

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posted on 2011-05-06, 00:00 authored by José Luis García Ruano, Esther Torrente, Ana M. Martín-Castro
Enantiomerically enriched α-aryl α-cyanoacetates and α-aryl α-acylacetonitriles bearing a benzylic quaternary stereocenter have been readily synthesized by stereoselective reaction of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different acylating and alkoxycarbonylating reagents under basic conditions. The stereoselectivity of the reactions proved closely dependent on the nature of the intermediate carbanionic species, the evolution of which was effectively controlled by a sulfinyl group as a remote chiral auxiliary.