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Synlett 1999; 1999(3): 348-350
DOI: 10.1055/s-1999-2604
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Dipolar [3+2] Cycloaddition Reactions with Planar Chiral Arene Tricarbonyl Chromium Complexes: Synthesis of Enantiopure Trisubstituted Pyrrolidines

Barbara Schnell* , Gérald Bernardinelli, E. P. Kündig
  • *Département de Chimie Organique, Université de Genève, 30 quai Ernest Ansermet, CH-12111 Genève 4, Switzerland; Fax +41 (22) 3 28 73 96; E-mail: Peter.Kundig@chiorg.unige.ch
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Publication Date:
31 December 1999 (online)

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Methyl acrylates and azomethine ylides linked to a planar chiral arene Cr(CO)3 complex underwent highly diastereoselective [3+2] cycloadditions with regioselectivities that could be controlled by the choice of the Lewis acid. Decomplexation yielded enantiopure pyrrolidines.

dipolar cycloaddition - planar chirality - arene complex - chromium - pyrrolidine

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