Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions

被引：24

作者：

Gabriela Avila-Ortiz, C. ^{[1
]}

Diaz-Corona, Lenin ^{[1
]}

Jimenez-Gonzalez, Erika ^{[1
]}

Juaristi, Eusebio ^{[1
,2
]}

机构：

[1] Ctr Invest & Estudios Avanzados, Dept Quim, Ave IPN 2508, Mexico City 07360, DF, Mexico

[2] El Colegio Nacl, Ctr Hist, Luis Gonzalez Obregon 23, Mexico City 07360, DF, Mexico

来源：

MOLECULES | 2017年 / 22卷 / 08期

关键词：

peptides; Michael addition; asymmetric organocatalysis; solvent-free reactions; CHIRAL PRIMARY AMINE; ENANTIOSELECTIVE CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; BIFUNCTIONAL ORGANOCATALYSTS; ALDOL REACTIONS; THIOUREA; NITROOLEFINS; DIPEPTIDES; KETONES; ISOBUTYRALDEHYDE;

D O I：

10.3390/molecules22081328

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The application of six novel alpha,beta-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins.

引用

页数：14

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