Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters

  • J Org Chem. 2017 Feb 17;82(4):2276-2280. doi: 10.1021/acs.joc.6b03059.
Jessica A Griswold  1 ,  Matthew A Horwitz  1 ,  Leslie V Leiva  1 ,  Jeffrey S Johnson  1
Affiliations
  • 1. Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
PMID: 28164699 DOI: 10.1021/acs.joc.6b03059
Abstract

A quinidine-catalyzed diastereoselective addition of α-angelica lactone to β-halo-α-ketoesters is reported. The α-angelica lactone displays unusual regioselectivity in this reaction, acting as a nucleophile at the α-position to provide fully substituted glycolic esters with three contiguous stereocenters. Subsequent diastereoselective hydrogenation provides an additional stereocenter within the lactone.

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