New Route to Chiral Amides

  • Author: ChemViews
  • Published Date: 29 October 2011
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Interest in the direct transformation of chiral secondary alcohols into new compound classes with retention of configuration is growing as non-racemic alcohols are becoming increasingly available. Most stereoselective approaches to amides from chiral alcohols require multistep procedures.

Salvatore Lepore and colleagues, Florida Atlantic University, USA, report a one-pot amidation reaction for cyclic alcohols that gives complete retention of configuration. They use a chlorosulfite leaving group formed in situ by reaction of the alcohol and thionyl chloride. The leaving group is chelated by a TiIV nitrile complex that is also generated in situ by reaction of TiF4 and alkyl or aryl nitrile.

One-pot, stereoretentive amidation of alcohols

The Ti nitrile complex is thought to chelate the chlorosulfite in the transition state to create a carbocation that is rapidly captured by the nitrile nucleophile through a front-side attack mechanism. This is the first experimental verification of secondary hyperconjomers, a theory of non-planar carbocations developed by Sorensen and Schleyer.

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH