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Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral alpha,beta-dihydroxy- or alpha,beta-gamma-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

Original publication

DOI

10.1039/B411724G

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/11/2004

Volume

2

Pages

3385 - 3400

Keywords

Aldehydes, Chemistry, Organic, Glycolates, Lactones, Models, Chemical, Stereoisomerism