期刊
CHEMICAL RECORD
卷 16, 期 6, 页码 2430-2448出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201500283
关键词
asymmetric catalysis; cycloaddition; enantioselectivity; ligand design; transition metals
资金
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ2004-00808/BQU, 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2010-20387, PHB2008-0037-PC]
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43446-P, CTQ2014-51912-REDC]
- FEDER
- Generalitat Valenciana [PROMETEO/2009/039, PROMETEOII/2014/017]
- University of Alicante
2,2'Bis(diphenylphosphino)-1,1'-binaphthyl (binap) and phosphoramidites are privileged chiral ligands that have been tested in the coinage-metal-catalyzed 1,3-dipolar cycloadditions of metalloazomethine ylides and electrophilic alkenes. Silver(I), copper(II), and gold(I) salts have been evaluated in all of these reactions. Maleimides, acrylates, fumarates, 1,2bis(phenylsulfonyl) ethylene, and enones reacted with imino esters to give the corresponding endoprolinates, such as hepatitis C (HCV) inhibitors, in high diastereo-and enantioselectivity using either binap-silver and -gold(I) or phosphoramidite-silver complexes. In the case of nitroalkenes, exo-4-nitroprolinates were obtained using silver or copper(II) phosphoramidite complexes. Azlactones reacted with maleimides and acrylates to give pyrrolines only in the presence of binapgold(I) complexes. The observed enantioselectivity and mechanism of these 1,3-dipolar cycloadditions were studied for the most relevant examples by means of DFT calculations.
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