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Enantioselective Synthesis of Polysubstituted Spiro-nitroprolinates Mediated by a (R,R)-Me-DuPhos·AgF-Catalyzed 1,3-Dipolar Cycloaddition

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Title: Enantioselective Synthesis of Polysubstituted Spiro-nitroprolinates Mediated by a (R,R)-Me-DuPhos·AgF-Catalyzed 1,3-Dipolar Cycloaddition
Authors: Cayuelas Rubio, Alberto | Ortiz, Ricardo | 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: Enantioselective | Cycloaddition
Knowledge Area: Química Orgánica
Issue Date: 8-Jun-2016
Publisher: American Chemical Society
Citation: Organic Letters. 2016, 18(12): 2926-2929. doi:10.1021/acs.orglett.6b01273
Abstract: The synthesis of constrained spirocycles is achieved effectively by means of 1,3-dipolar cyclodditions employing α-imino γ-lactones as azomethine ylide precursors and nitroalkenes as dipolarophiles. The complex formed by (R,R)-Me-DuPhos 18 and AgF is the most efficient bifunctional catalyst. Final spiro-nitroprolinates cycloadducts are obtained in good to moderate yields and both high diastereo- and enantioselectivities. Density functional theory (DFT) calculations supported the expected absolute configuration as well as other stereochemical parameters.
Sponsor: Financial support was provided by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (Projects CTQ2013-43446-P, and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), the University of Alicante, the Gobierno Vasco/Eusko Jaurlaritza (Grant IT673-13), and the University of the Basque Country UPV/EHU (UFI11/22 QOSYC). O.L. gratefully acknowledges the UPV/EHU for her postdoctoral grant.
URI: http://hdl.handle.net/10045/56250
ISSN: 1523-7060 (Print) | 1523-7052 (Online)
DOI: 10.1021/acs.orglett.6b01273
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2016 American Chemical Society
Peer Review: si
Publisher version: http://dx.doi.org/10.1021/acs.orglett.6b01273
Appears in Collections:INV - SINTAS - Artículos de Revistas

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