Chiral N,N′-dioxide/Mg(OTf)2 complex-catalyzed asymmetric [2,3]-rearrangement of in situ generated ammonium salts

被引:15
|
作者
Lin, Qianchi [1 ]
Hu, Bowen [1 ]
Xu, Xi [1 ]
Dong, Shunxi [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; STEVENS REARRANGEMENT; ALLYLIC AMINATION; DERIVATIVES; PEPTIDES; LIGANDS; YLIDES;
D O I
10.1039/c9sc06342k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic enantioselective [2,3]-rearrangements of in situ generated ammonium ylides from glycine pyrazoleamides and allyl bromides were achieved by employing a chiral N,N '-dioxide/Mg-II complex as the catalyst. This protocol provided a facile and efficient synthesis route to a series of anti-alpha-amino acid derivatives in good yields with high stereoselectivities. Moreover, a possible catalytic cycle was proposed to illustrate the reaction process and the origin of stereoselectivity.
引用
收藏
页码:3068 / 3073
页数:6
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