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用于轴向手性苯甲酰胺不对称合成的双功能有机催化剂。

Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

作者信息

Miyaji Ryota, Wada Yuuki, Matsumoto Akira, Asano Keisuke, Matsubara Seijiro

机构信息

Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan.

出版信息

Beilstein J Org Chem. 2017 Aug 2;13:1518-1523. doi: 10.3762/bjoc.13.151. eCollection 2017.

DOI:10.3762/bjoc.13.151
PMID:28845196
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5550815/
Abstract

Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatility of bifunctional organocatalysts for the enantioselective construction of axially chiral compounds. Moderate to good enantioselectivities were afforded with a range of benzamide substrates. Mechanistic investigations were also carried out.

摘要

在手性分子骨架中带有氨基和脲官能团的双功能有机催化剂被应用于通过芳香亲电溴化对轴向手性苯甲酰胺进行对映选择性合成。结果证明了双功能有机催化剂在轴向手性化合物对映选择性构建方面的多功能性。一系列苯甲酰胺底物获得了中等至良好的对映选择性。还进行了机理研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/34b58da61df6/Beilstein_J_Org_Chem-13-1518-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/bfde6da7a9b2/Beilstein_J_Org_Chem-13-1518-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/a1098e2374ea/Beilstein_J_Org_Chem-13-1518-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/34b58da61df6/Beilstein_J_Org_Chem-13-1518-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/bfde6da7a9b2/Beilstein_J_Org_Chem-13-1518-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/a1098e2374ea/Beilstein_J_Org_Chem-13-1518-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/02fb/5550815/34b58da61df6/Beilstein_J_Org_Chem-13-1518-g007.jpg

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