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Synlett 1997; 1997(5): 615-617
DOI: 10.1055/s-1997-3221
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Stereocontrolled Synthesis of (E)-Olefin Dipeptide Isosteres using a [3,3] Allylic Trichloracetimidate Rearrangement

Hassan Imogaï, Yves Petit, Marc Larchevêque*
  • *Laboratoire de Synthèse Organique associé au CNRS, ENSCP, 11 rue Pierre et Marie Curie, 75231 - Paris Cedex 05, France, Fax 01 43 25 79 75
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Publikationsdatum:
31. Dezember 2000 (online)

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The addition of Z-vinylic cuprates to enantiopure α-alkyl β-alkoxy aldehydes afforded syn allylic monoprotected diols in high diastereomerical purity. The sigmatropic rearrangement of trichloracetimidates derived from these monoprotected diols afforded protected allylic aminoalcohols which were oxidized into E-Alkene dipeptide isosteres.

1,2-induction - allylic amine - chirality transfer