Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides

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Title: Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides
Authors: Vizcaíno-Milla, Pascuala | Sansano, Jose M. | Nájera, Carmen | Fiser, Béla | Gómez Bengoa, Enrique
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: Asymmetric organocatalysis | Maleimides | Succinimides | Aldehydes | Michael addition
Knowledge Area: Química Orgánica
Issue Date: 26-May-2015
Publisher: Georg Thieme Verlag
Citation: Synthesis. 2015, 47(15): 2199-2206. doi:10.1055/s-0034-1380718
Abstract: Chiral primary amines containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a pyrimidin-2-yl unit are synthesized and used as general organocatalysts for the Michael reaction of α-branched aldehydes to maleimides. The reaction takes place with 10 mol% organocatalyst loading and hexanedioic acid as cocatalyst in aqueous N,N-dimethylformamide at 10 °C affording the corresponding succinimides in good yields and enantioselectivities. DFT calculations support the stereochemical results and the role played by the solvents.
Sponsor: The Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economia y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), the Basque Government (GV Grant IT-291-07), the FP7 Marie Curie Actions of the European Commission via the ITN ECHONET network (MCITN-2012-316379), and the Universities of Alicante and Basque Country are gratefully acknowledged for financial support.
URI: http://hdl.handle.net/10045/48658
ISSN: 0039-7881 (Print) | 1437-210X (Online)
DOI: 10.1055/s-0034-1380718
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-0034-1380718
Appears in Collections:INV - SINTAS - Artículos de Revistas
Research funded by the EU

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