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

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.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Sanganee, HJ More by this author
Szolcsanyi, P More by this author
Journal:
TETRAHEDRON
Volume:
55
Issue:
11
Pages:
3337-3354
Publication date:
1999-03-12
DOI:
ISSN:
0040-4020
URN:
uuid:c187967f-30f7-47a1-b658-715dd6895418
Source identifiers:
110619
Local pid:
pubs:110619
Language:
English

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