Metal-free and enantioselective synthesis of 1,4-benzoxazepines from para-quinone methide derivatives and α-bromohydroxamates

被引：4
|
作者：
Qi, Suo-Suo [1 ]
Luo, Xin [1 ]
Sun, Xiao-Ping [1 ]
Zhai, Jing-Jing [1 ]
Chu, Ming-Ming [2 ]
Chen, Jin [3 ]
Wang, Yi-Feng [1 ]
Xu, Dan-Qian [1 ]
机构：
[1] Zhejiang Univ Technol, Dept Green Chem & Technol, State Key Lab Breeding Base Green Chem Synth Techn, Key Lab Green Pesticides & Cleaner Prod Technol Zh, Hangzhou 310014, Peoples R China
[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Peoples R China
[3] Inst Chem Co Ltd, Henan Acad Sci, Zhengzhou 450002, Henan, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 57期
关键词：
ACCESS; CYCLIZATION; ANNULATION; AZIRIDINES; CHROMANS;
D O I：
10.1039/d3cc02368k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A sequential asymmetric conjugate addition/cyclisation of & alpha;-bromohydroxamates with para-quinone methide derivatives has been developed, which provides enantioenriched 1,4-benzoxazepines in generally high yields (up to 95%) and good enantioselectivities (up to 97 : 3 er). This protocol not only offers a novel and straightforward strategy for constructing chiral 1,4-benzoxazepines, but also demonstrates the potential of & alpha;-bromohydroxamates as three-atom synthons in asymmetric cyclisation reactions.
引用
收藏
页码：8822 / 8825
页数：4
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