BINAP-AgSbF6 vs. BINAP-AgClO4 Complexes as Catalysts for the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes

Abstract The employment of AgSbF 6 and BINAP ligands has been evaluated in the catalyzed enantioselective 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes. The results are compared with the analogous ones obtained when using AgClO 4 . The cycloaddition with maleimides a...

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Published in:Synlett 2010-04, Vol.2010 (6), p.962-966
Main Authors: Martín-Rodríguez, María, Nájera, Carmen, Sansano, José M., Costa, Paulo R., de Lima, Evanoel Crizanto, Dias, Ayres G.
Format: Article
Language:English
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Summary:Abstract The employment of AgSbF 6 and BINAP ligands has been evaluated in the catalyzed enantioselective 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes. The results are compared with the analogous ones obtained when using AgClO 4 . The cycloaddition with maleimides and TRANS-1,2-bis(phenylsulfonyl)ethylene are clearly improved by the AgSbF 6 -derived catalyst, and its efficiency is crucial for ensure good yields and excellent ee in the three-component reaction.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1219534