Catalytic enantioselective synthesis of azacycloalkenes via intermolecular rhodium carbenoid C–H insertion/ring-closing metathesis sequence

Enantiomerically enriched cyclopropanes and products of C–H insertion reactions were obtained in excellent combined yields and enantioselectivities as a consequence of rhodium-catalyzed decomposition of vinyl diazoacetate in the presence of tert-butoxycarbonyl-(Boc)-protected amines as trapping agen...

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Bibliographic Details
Published in:Tetrahedron letters 2012-02, Vol.53 (7), p.849-851
Main Authors: McMills, Mark C., Humes, Ross J., Pavlyuk, Oksana M.
Format: Article
Language:English
Subjects:
Azacycle
C–H insertion
Diazo
Metathesis
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Summary:Enantiomerically enriched cyclopropanes and products of C–H insertion reactions were obtained in excellent combined yields and enantioselectivities as a consequence of rhodium-catalyzed decomposition of vinyl diazoacetate in the presence of tert-butoxycarbonyl-(Boc)-protected amines as trapping agents. A series of enantiomerically enriched six- to eight-membered nitrogen-containing heterocycles were subsequently prepared via ring-closing metathesis of the dienes catalyzed by ruthenium benzylidene complex.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.12.019