Journal
TETRAHEDRON-ASYMMETRY
Volume 23, Issue 22-23, Pages 1596-1606Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2012.10.015
Keywords
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) through the Hispano-Brazilian project [PHB2008-0037-PC, CNPq-2878]
- Consolider INGENIO [CSD2007-00006, CTQ2010-20387]
- FEDER
- Generalitat Valenciana [PROMETEO/2009/039]
- University of Alicante
- MEC
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Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfonyl)ethylene are suitable dipolarophiles for obtaining very good enantioselectivities, even better values are generated by a multicomponent version. There are some very interesting applications of the disulfonylated cycloadducts in the total synthesis of cis-2,5-disubstituted pyrrolidines, precursors of natural products, or valuable intermediates in the synthesis of antiviral compounds. (C) 2012 Elsevier Ltd. All rights reserved.
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