Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection

被引：12
作者：
Zheng, Yu [1 ]
Wang, Jing [1 ]
Xia, Peng-Ju [1 ]
Zhao, Qing-lan [1 ]
Xiao, Jun-An [2 ]
Xiang, Hao-Yue [1 ]
Chen, Xiao-Qing [1 ]
Yang, Hua [1 ]
机构：
[1] Cent S Univ, Coll Chem & Chem Engn, Changsha 410083, Hunan, Peoples R China
[2] Guangxi Teachers Educ Univ, Coll Chem & Mat Sci, Nanning 530001, Guangxi, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期
基金：
中国国家自然科学基金;
关键词：
HIGHLY ENANTIOSELECTIVE CONSTRUCTION; ONE-POT SYNTHESIS; AZOMETHINE YLIDES; CONJUGATE ADDITION; 1,3-DIPOLAR CYCLOADDITION; GAMMA-BUTENOLIDES; ACID DERIVATIVES; PHOSPHINE OXIDES; 3+2 ANNULATION; CYCLIC ENONES;
D O I：
10.1021/acs.joc.7b02064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
With the aid of in situ protection by N-(2-formylphenyl)-4-methyl-benzenesulfonamide, enantioselective allylic alkylation of Morita-Baylis-Hillman carbonates with diethyl 2-aminomalonate was successfully realized. The corresponding adducts can be obtained in up to 99% yield with up to 98% ee as well as excellent regioselectivity. Besides, the adducts with opposite configurations were readily prepared by utilizing easily available and inexpensive quinine or quinidine as organocatalyst. Facile deprotection of the resulting adduct provides straightforward access to enantiopure alpha-methylene-gamma-lactam.
引用
收藏
页码：12202 / 12208
页数：7
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