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Synfacts 2006(5): 0435-0435  
DOI: 10.1055/s-2006-934375
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

(-)-Sparteine-Mediated Asymmetric Synthesis of Polysubstituted Azepanes

Contributor(s): Victor Snieckus, Sunny Lai, Wei Gan
S. J. Lee, P. Beak*
University of Illinois at Urbana-Champaign, USA
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Publikationsdatum:
21. April 2006 (online)

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Significance

A general asymmetric synthesis of substituted azepanes with three and four stereocenters in high diastereo- and enantioselectivity is reported. The key step involves the generation of diastereoenriched and enantioenriched ene­carbamates 1 via (-)-sparteine-mediated asymmetric lithiation-conjugate addition, from which 4,5,6- and 3,4,5,6-substituted azepanes are synthesized stereoselectively in three and five steps, respectively, in good to excellent overall yields.