Enantioselective Synthesis of exo-4-Nitroprolinates from Nitroalkenes and Azomethine Ylides Catalyzed by Chiral Phosphoramidite·Silver(I) or Copper(II) Complexes
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Title: | Enantioselective Synthesis of exo-4-Nitroprolinates from Nitroalkenes and Azomethine Ylides Catalyzed by Chiral Phosphoramidite·Silver(I) or Copper(II) Complexes |
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Authors: | Castelló Moncayo, Luis Miguel | Nájera, Carmen | Sansano, Jose M. | Larrañaga Agirre, Olatz | Cózar Ruano, Abel de | Cossío Mora, Fernando Pedro |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Dipolar cycloaddition | Asymmetric catalysis | Azomethine ylides | Phosphoramidite | Copper | Silver |
Knowledge Area: | Química Orgánica |
Issue Date: | 19-Feb-2015 |
Publisher: | Georg Thieme Verlag |
Citation: | Synthesis. 2015, 47(07): 934-943. doi:10.1055/s-0034-1380158 |
Abstract: | 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 α-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. |
Sponsor: | This work has been supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2010-20387) and Ministerio de Economía y Competitvidad (MINECO) (CTQ2013-43446P, CTQ2014-51912-REDC), FEDER, Generalitat Valenciana (PROMETEO/2009/039 and 2014/017), and by the University of Alicante. L.M.C. thanks the MICINN for a FPI fellowship. Financial support was also provided by the MICINN and FEDER (projects CTQ2010-16959/BQU), the University of the Basque Country (UPV/EHU, UFI11/22QOSYC) and the Basque Government (GV/EJ, grant IT-324-07). |
URI: | http://hdl.handle.net/10045/46122 |
ISSN: | 0039-7881 (Print) | 1437-210X (Online) |
DOI: | 10.1055/s-0034-1380158 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © Georg Thieme Verlag Stuttgart · New York |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1055/s-0034-1380158 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
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2015_Castello_etal_Synthesis_final.pdf | Versión final (acceso restringido) | 253,81 kB | Adobe PDF | Open Request a copy |
2015_Castello_etal_Synthesis_rev.pdf | Versión revisada (acceso abierto) | 236,76 kB | Adobe PDF | Open Preview |
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