Boron trifluoride-mediated synthesis of N-aryl-substituted pyrrolidines from tetrahydrofuran and amines

被引：9
|
作者：
Hu, Shanshan [1 ,2 ]
Huo, Yan [1 ,2 ]
Wang, Zhihong [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, 94 Weijin Rd, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, 94 Weijin Rd, Tianjin 300071, Peoples R China
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2017年 / 53卷 / 12期
关键词：
N-aryl-substituted pyrrolidines; cyclic ether; Lewis acid; tetrahydrofuran activation; ring opening; AMINATION; HETEROCYCLIZATION; ALKYLATION; SECONDARY; AZACYCLES; ALCOHOLS;
D O I：
10.1007/s10593-018-2220-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Boron trifluoride-mediated transformation of tetrahydrofuran to corresponding N-aryl-substituted pyrrolidines is conducted under mild reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing process as the rate-determining step.
引用
收藏
页码：1365 / 1368
页数：4
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