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Synthesis 2000; 2000(7): 935-940
DOI: 10.1055/s-2000-6306
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The Reaction of Chromium Alkenyl Carbene Complexes with Alkenyl Oxazolines: A Diastereoselective [3 + 2] Annulation Route to Cyclopentanones

José Barluenga* , Miguel Tomás, Angel L. Suárez-Sobrino
  • *Instituto Universitario de Química Organometálica "Enrique Moles", Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, E-33071 Oviedo, Spain; Fax +34(98)5103450; E-mail: barluenga@sauron.quimica.uniovi.es
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Publication Date:
31 December 2000 (online)

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Pentacarbonyl(alkenylmethoxy)carbene chromium complexes 1 undergo regio- and diastereoselective formal [3 + 2] cycloaddition to electron-deficient alkenes, e.g. alkenyl oxazoline derivatives 2, affording cyclopentanoids 3 and 4, the cis isomer 3 being the major stereoisomer. The cyclopropane intermediates 5/6 were isolated, under appropriate reaction conditions, and further converted into 3 and 4. The cycloadduct 3b was efficiently elaborated into the 3,4-disubstituted cyclopentanones 10 and 11.

[3 + 2] annulation - carbene complexes - chromium - stereoselective synthesis - cyclopentanone - cycloadditions

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