DBU-catalyzed Michael additions of bulky glycine imine to β-arylfuryl substituted α, β-unsaturated esters

被引：0

作者：

Cheng, Mei-Ling ^{[1
]}

Wang, Xue-Ying ^{[1
]}

Bai, Yu-Jun ^{[2
]}

Zhu, Si-Kai ^{[1
]}

Zhang, Sheng-Yong ^{[1
]}

Bao, Guo-Qiang ^{[3
]}

Wang, Ping-An ^{[1
]}

机构：

[1] AF Mil Med Univ, Sch Pharm, Dept Med Chem & Pharmaceut Anal, Xian, Peoples R China

[2] Northwest Univ, Coll Life Sci, Key Lab Resource Biol & Biotechnol Western China, Minist Educ, Xian, Peoples R China

[3] AF Mil Med Univ, Tangdu Hosp, Dept Gen Surg, Xian, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2023年 / 53卷 / 19期

基金：

中国国家自然科学基金;

关键词：

alpha; beta-unsaturated ester; DBU; glycine imine; Michael addition; pyroglutamic acid; CONJUGATE ADDITION; DERIVATIVES; COMPLEXES; ACIDS;

D O I：

10.1080/00397911.2023.2240450

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DBU-catalyzed Michael reactions between tert-butyl 2-((diphenyl-methylene) amino)acetate and simple beta-substituted alpha, beta-unsaturated esters have been achieved in high yields (up to 95% yield) and diastereoselectivties (up to 99:1 dr) in the presence of 1.0 eq. of LiBr in acetonitrile under room temperature. The Michael adduct can be easily converted into trans-3-substituted pyroglutamic acid ester through in-situ acidic hydrolysis following lactamation. [GRAPHICS] .

引用

页码：1637 / 1646

页数：10

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