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Synlett 1998; 1998(3): 275-276
DOI: 10.1055/s-1998-1624
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Enantioselective Synthesis of α-Methylene-γ-Lactams. Nucleophilic Addition of a Chirally Modified β-Functionalized Allylboronate Reagent to Imines

Isabelle Chataigner* , Françoise Zammattio, Jacques Lebreton, Jean Villiéras
  • *Laboratoire de Synthèse Organique, CNRS UMR 6513, Faculté des Sciences et des Techniques de Nantes, BP 92208, 2 rue de la Houssinière, 44322 Nantes Cedex 3, France; Fax (33) 2.40.74.50.00; E-mail: villiera@chimie.univ-nantes.fr
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Publication Date:
31 December 2000 (online)

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The reaction of β-functionalized allylboronate 1 derived from endo-2-phenyl-exo-2,3-bornanediol with imines affords homoallylic amines and α-methylene-γ-lactams in good yields and high enantioselectivity (ee ≥94%). A mechanism of the carbalkoxyallylboration reaction is proposed to explain the excellent asymmetric induction.

chiral β-functionalized allylboronate - endo-2-phenyl-exo-2,3-bornanediol - α-trimethylsilyl-imines - α-methylene-γ-lactams - homoallylic amines

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