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(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D- phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (-)-Aplysillamide B.

Original publication

DOI

10.1016/S0040-4020(98)01145-4

Type

Journal article

Journal

Tetrahedron

Publication Date

01/03/1999

Volume

55

Pages

3337 - 3354