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无溶剂反应条件下 α,β-二肽催化不对称 Michael 加成反应。

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

机构信息

Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN 2508, Ciudad de México 07360, Mexico.

El Colegio Nacional, Luis González Obregón 23, Centro Histórico, Ciudad de México 06020, Mexico.

出版信息

Molecules. 2017 Aug 10;22(8):1328. doi: 10.3390/molecules22081328.

DOI:10.3390/molecules22081328
PMID:28796165
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6152315/
Abstract

The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and -arylmaleimides or nitroolefins is described. With -arylmaleimides as substrates, the best results were achieved with dipeptide as a catalyst in the presence of aq. NaOH. Whereas dipeptides and 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.

摘要

六种新型的α,β-二肽作为手性有机催化剂在烯醇醛和芳基马来酰亚胺或硝基烯烃的不对称迈克尔加成反应中的应用被描述。以芳基马来酰亚胺作为底物,当使用 aq. NaOH 作为催化剂时,二肽 获得了最好的结果。而二肽 和 与 4-二甲氨基吡啶(DMAP)和硫脲结合作为氢键供体,在异丁醛和各种硝基烯烃之间的对映选择性反应中被证明是高效的有机催化体系。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/5338d5e095f6/molecules-22-01328-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/cdc36eb478b6/molecules-22-01328-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/9a197dbb5a90/molecules-22-01328-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/83c858c1fd58/molecules-22-01328-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/3185180155f0/molecules-22-01328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/bd73a421267d/molecules-22-01328-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/5338d5e095f6/molecules-22-01328-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/cdc36eb478b6/molecules-22-01328-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/9a197dbb5a90/molecules-22-01328-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/83c858c1fd58/molecules-22-01328-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/3185180155f0/molecules-22-01328-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/bd73a421267d/molecules-22-01328-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41de/6152315/5338d5e095f6/molecules-22-01328-sch004.jpg

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