One-pot synthesis of -lactams by the Ugi and Michael addition cascade reaction

被引：24

作者：

Gao, Xing ^{[1
]}

Shan, Chunhui ^{[2
]}

Chen, Zhihao ^{[1
]}

Liu, Yan ^{[1
]}

Zhao, Xia ^{[3
]}

Zhang, Ao ^{[1
]}

Yu, Peng ^{[1
]}

Galons, Herve ^{[1
]}

Lan, Yu ^{[2
]}

Lu, Kui ^{[1
]}

机构：

[1] Tianjin Univ Sci & Technol, Tianjin Int Cooperat Res Ctr Food Nutr Safety & M, China Int Sci & Technol Cooperat Base Food Nutr S, Coll Biotechnol, Tianjin 300457, Peoples R China

[2] Univ Chongqing, Sch Chem & Chem Engn Chongqing, Chongqing 400030, Peoples R China

[3] Tianjin Normal Univ, Coll Chem, Tianjin 300387, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 33期

基金：

美国国家科学基金会;

关键词：

DIVERSITY-ORIENTED SYNTHESIS; BETA-LACTAMS; CYCLIZATION; ACIDS;

D O I：

10.1039/c8ob01176a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diversity-oriented synthesis of -lactams was achieved via Ugi/Michael reaction cascades under mild conditions. The intramolecular hydrogen bonding between the heteroatom from an aldehyde component and the amide NH group controls the chemoselectivity of the Michael reaction versus the aza-Michael reaction. DFT calculation was performed to clarify the mechanism, chemo-selectivity and diastereoselectivity of this work. This one-pot protocol offers a straightforward method to build a diversified -lactam library for drug discovery.

引用

收藏

页码：6096 / 6105

页数：10

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