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Synthesis 2000; 2000(7): 985-989
DOI: 10.1055/s-2000-6300
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First Example of a Total Axial to Centered Chirality Transfer in the [2 + 2 + 2] Cycloadditions of Allenediynes

Olivier Buisine* , Corinne Aubert, Max Malacria
  • *Université P. et M. Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44 - 54, B. 229, 4, Place Jussieu, 75252 Paris Cedex, France; Fax (33)0144277360; E-mail: malacria@ccr.jussieu.fr
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Publication Date:
31 December 2000 (online)

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The cobalt-mediated [2 + 2 + 2] cycloaddition of allenediynes bearing a phosphine oxide group at one alkyne terminus is a completely regio-, chemo- and diastereoselective high yielding process. Moreover, a total transfer of chiral information from axial to centered chirality is evident, which makes this reaction a new and powerful tool for the preparation of enantiomerically enriched tricyclic derivatives.

alkynes - allenes - chirality - cycloadditions - cobalt

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