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Synthesis 2000; 2000(12): 1689-1694
DOI: 10.1055/s-2000-8199
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Diastereoselective Conjugate Additions to t-Leucine-Derived N-Enoyl 1,3-Oxazolidin-2-ones

Christoph Schneider* , Oliver Reese
  • *Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany; Fax +49 (5 51) 39 96 60; E-mail: cschnei1@gwdg.de
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Publication Date:
31 December 2000 (online)

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Conjugate addition reactions of cuprate reagents to t-leucine-derived N-enoyl 1,3-oxazolidin-2-ones proceed with high diastereofacial differentiation. Additional functional groups in the substrates like enoate, acetal, and hydrazone moieties are readily tolerated.

conjugate addition - cuprates - asymmetric synthesis - 1,3-oxazolidin-2-ones - Cope rearrangement - Lewis acid