Fast Assignment

  • Author: David Bradley
  • Published: 27 July 2011
  • Copyright: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic Letters/ACS
thumbnail image: Fast Assignment

Obtaining the absolute configuration of a natural product or new organic molecule is a critical stage in characterization and development of synthetic strategies. Unfortunately, the standard approach, the Mosher method, while powerful, requires formation of a secondary alcohol that is relatively unhindered sterically. Moreover, the ester must be stable and amenable to isolation.

Now, a more general method that uses a chiral catalyst, Birman's S-HBTM and R-HBTM, to acylate the secondary alcohol derivative of each enantiomer offers a more straightforward approach. NMR spectroscopy and kinetics of the two reactions are compared with library structures.

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