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

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2017 Feb 7

PMID 28164699

Citations 3

Authors

Jessica A Griswold

Matthew A Horwitz

Leslie V Leiva

Jeffrey S Johnson

Affiliations

Soon will be listed here.

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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