Asymmetric hetero Diels-Alder as an access to carbacephams

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  4. Corzana, F. 1
  5. Peregrina, J.M. 1
  6. Zurbano, M.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Journal:
Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2002

Volume: 67

Issue: 2

Pages: 598-601

Type: Article

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DOI: 10.1021/JO016186H PMID: 11798338 SCOPUS: 2-s2.0-0037169120 WoS: WOS:000173480500037 GOOGLE SCHOLAR

More publications in: Journal of Organic Chemistry

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Abstract

A short and efficient asymmetric synthesis of the (6R,7S)-7-tert-butoxycarbonylamino-2-ketocarbacepham is described. The key step involves the hetero Diels-Alder reaction of the benzylimine derived from the enantiomer of Garner's aldehyde with Danishefsky's diene.