Tetrahedron

The 'SuperQuat'(R)-4-phenyl-5, 5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (−)-Aplysillamide B

SG Davies, HJ Sanganee, P Szolcsanyi

Index: Davies, Stephen G.; Sanganee, Hitesh J.; Szolcsanyi, Peter Tetrahedron, 1999 , vol. 55, # 11 p. 3337 - 3354

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Citation Number: 70

Abstract

(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.

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