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

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.

SUBMITTER: Griswold JA 

PROVIDER: S-EPMC5324730 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature