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

Pascuala Vízcaíno-Milla; José M. Sansano; Carmen Nájera; Béla Fiser; Enrique Gómez-Bengoa

doi:10.1055/s-0034-1380718

Synthesis, Table of Contents

Synthesis 2015; 47(15): 2199-2206
DOI: 10.1055/s-0034-1380718

special topic

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

Pascuala Vízcaíno-Milla

^aDepartamento de Química Orgánica and Centro de Innovación, en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain Email: cnajera@ua.es

,

José M. Sansano

^aDepartamento de Química Orgánica and Centro de Innovación, en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain Email: cnajera@ua.es

,

Carmen Nájera*

^aDepartamento de Química Orgánica and Centro de Innovación, en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain Email: cnajera@ua.es

,

Béla Fiser

^bDepartmento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain Email: enrique.gomez@ehu.es

,

Enrique Gómez-Bengoa*

^bDepartmento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain Email: enrique.gomez@ehu.es

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Abstract

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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.

Key words

asymmetric organocatalysis - maleimides - succinimides - aldehydes - Michael addition

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References

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