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
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
收藏
页码:1637 / 1646
页数:10
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