Hydrogen-Bond-Directed Enantioselective Decarboxylative Mannich Reaction of -Ketoacids with Ketimines: Application to the Synthesis of Anti-HIV Drug DPC083

被引：143

作者：

Yuan, Hai-Na ^{[1
]}

Wang, Shuai ^{[1
]}

Nie, Jing ^{[1
]}

Meng, Wei ^{[1
]}

Yao, Qingwei ^{[2
]}

Ma, Jun-An ^{[1
]}

机构：

[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China

[2] Sphinx Sci Lab Corp, Sycamore, IL 60178 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 14期

关键词：

enantioselectivity; heterocycles; ketimines; organocatalysis; synthetic methodology; BETA-KETO ACIDS; ASYMMETRIC CATALYSIS; MICHAEL ADDITION; AROMATIC KETONES; ALDOL REACTION; TRIFLUOROMETHYLATION; ALKALOIDS; BIOSYNTHESIS; CONSTRUCTION; SACCHARIDES;

D O I：

10.1002/anie.201210361

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Key to success: The title reaction provides facile access to enantioenriched 3,4-dihydroquinazolin-2(1H)-ones containing a quaternary stereogenic center in high yields with excellent enantioselectivities. Subsequent transformations lead to the convenient preparation of the anti-HIV drug DPC 083 and N-fused polycyclic compounds without loss of enantiomeric excess. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3869 / 3873

页数：5

共 3 条

[1] Highly Enantioselective Decarboxylative Mannich Reaction of Malonic Acid Half Oxyesters with Cyclic Trifluoromethyl Ketimines: Synthesis of β-Amino Esters and Anti-HIV Drug DPC 083
Yuan, Hai-Na
Li, Shen
Nie, Jing
Zheng, Yan
Ma, Jun-An
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) : 15856 - 15860
[2] Bifunctional Cinchona Alkaloid Thiourea Catalyzed Highly Efficient, Enantioselective Aza-Henry Reaction of Cyclic Trifluoromethyl Ketimines: Synthesis of Anti-HIV Drug DPC 083
Xie, Hexin
Zhang, Yinan
Zhang, Shilei
Chen, Xiaobei
Wang, Wei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) : 11773 - 11776
[3] Highly enantioselective organocatalytic Strecker reaction of cyclic N-acyl trifluoromethylketimines: synthesis of anti-HIV drug DPC 083
Zhang, Fa-Guang
Zhu, Xiao-Yan
Li, Shen
Nie, Jing
Ma, Jun-An
CHEMICAL COMMUNICATIONS, 2012, 48 (94) : 11552 - 11554

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