Synthesis of methyl 2-exo-cyano-3-exo-phenyl-5,6-endo (or exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates in enantiomerically pure form

  1. Cativiela, C. 1
  2. Avenoza, A. 2
  3. Peregrina, J.M. 2
  1. 1 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Journal:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Year of publication: 1993

Volume: 4

Issue: 7

Pages: 1677-1682

Type: Article

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DOI: 10.1016/S0957-4166(00)80375-4 SCOPUS: 2-s2.0-0027303850 WoS: WOS:A1993LK75500052 GOOGLE SCHOLAR

More publications in: Tetrahedron: Asymmetry

Abstract

The enantiomers (1R, 2R, 3S, 4S, 5S, 6S) and (1S, 2S, 3R, 4R, 5R, 6R) of the 2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo[2.2.1]heptan e-2-endo-carboxylic acid lactone 4 and 5, obtained starting from the endo-cycloadducts of the asymmetric Diels-Alder reactions between cyclopentadiene and (E)-2-cyanocinnamates of (R)-pantolactone 2 and (S)-ethyl lactate 3, are converted into the methyl 2-exo-cyano-3-exo-phenyl-5,6-endo(and exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates 6, 7, 8 and 9 in enantiomerically pure form.