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Synlett 1991; 1991(6): 417-419
DOI: 10.1055/s-1991-20748
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Asymmetric Hetero-Diels-Alder Cycloadditions Using a Chiral N-Dienyl Lactam and Acylnitroso Dienophiles

Albert Defoin* , Joaquim Pires, Jacques Streith
  • *Ecole Nationale Supérieure de Chimie, Université de Haute-Alsace, 3 rue Alfred Werner, F-68093 Mulhouse Cedex, France
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Publication Date:
07 March 2002 (online)

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The (S)-N-(1,3-butadienyl)pyroglutamate methyl ester 2a [methyl (S)-1-(1,3-butadienyl)-5-oxo-2-pyrrolidinecarboxylate], when reacted with a series of acylnitroso dienophiles 3, gave regiospecifically the primary Diels-Alder adducts 4 and 5 [2-substituted (6S)- and (6R)-6-{(S)-2-methoxycarbonyl-5-oxo-1-pyrrolidinyl}-3,6-dihydro-2H-1,2-oxazines]. The major cyclo-adducts 4 appear in their (6S) configuration as determined by an X-ray analysis. The asymmetric pyroglutamate inductor was easily recovered by catalytic hydrogenolysis.

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