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Synfacts 2006(6): 0549-0549  
DOI: 10.1055/s-2006-934466
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Dearomatization Route to Cyclohexadienone Spirolactams

Contributor(s): Victor Snieckus, Bärbel Wittel
F. C. Pigge*, J. J. Coniglio, R. Dalvi
University of Iowa, Iowa City and University of Missouri, St. Louis, USA
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

An interesting combined ruthe­nium complex mediated dearomatization-Horner-Wardsworth-Emmons route to cyclohexa­diene spirolactams is reported. The reactions proceed in good yields using several aliphatic and aromatic aldehydes leading to products with exclusive (Z)-configuration. The oxidative decomplexation is achieved using copper(II) salts to give either azaspirocyclic dienones or hydroxy-substituted dienes as a function of the R2 substituent.