Journal
SYNTHESIS-STUTTGART
Volume 47, Issue 7, Pages 934-943Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1380158
Keywords
dipolar cycloaddition; asymmetric catalysis; azomethine ylides; phosphoramidite; copper; silver
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [INGENIO 2010 CSD2007-00006, CTQ2010-20387]
- Ministerio de Economia y Competitvidad (MINECO) [CTQ2013-43446P, CTQ2014-51912-REDC]
- FEDER, Generalitat Valenciana [PROMETEO/2009/039, 2014/017]
- University of Alicante
- MICINN
- FEDER [CTQ2010-16959/BQU]
- University of the Basque Country (UPV/EHU) [UFI11/22QOSYC]
- Basque Government (GV/EJ) [IT-324-07]
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Chiral complexes formed by privileged phosphoramidites derived from chiral binol and optically pure Davies' amines, and copper(II) triflate, silver(I) triflate or silver(I) benzoate are excellent catalysts for the general 1,3-dipolar cycloaddition between nitroalkenes and azomethine ylides generated from -amino acid derived imino esters. These three methods can be conducted at room temperature to afford the exo-cycloadducts (4,5-trans-2,5-cis-4-nitroprolinates) with high diastereoselectivity and high enantioselectivity. In general, the three procedures are complementary but silver catalysts are more versatile and less sensitive to sterically congested starting materials.
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