Diastereoselective enzymatic synthesis of highly substituted 3,4-dihydropyridin-2-ones via domino Knoevenagel condensation-Michael addition-intramolecular cyclization

被引：32
作者：
Liu, Zhi-Qiang [1 ]
Liu, Bo-Kai [1 ]
Wu, Qi [1 ]
Lin, Xian-Fu [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 50期
基金：
中国国家自然科学基金;
关键词：
Acylase; 3,4-Dihydropyridin-2-ones; Three-component; Cyanoacetamide; Diastereoselective; REVERSE-TRANSCRIPTASE INHIBITORS; CARBON BOND FORMATION; CATALYTIC PROMISCUITY; BIOLOGICAL EVALUATION; DERIVATIVES; ENZYMES; LIPASE; DIHYDROPYRIDINONE; PATHWAYS; MEDIA;
D O I：
10.1016/j.tet.2011.09.086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct method to construct 3,4-dihydropyridin-2-ones by enzymatic condensation of aldehyde with cyanoacetamide and 1,3-dicarbonyl compounds was developed. One ring and four new bonds (two C-C, one C-N, one C=C) were formed in one pot. And reaction conditions involving hydrolases, solvents, substrate molar ratios, and hydrolase loading were optimized. A series of new compounds based on the 3,4-dihydropyridin-2-one core were synthesized by the unprecedented three-component domino reaction. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9736 / 9740
页数：5
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