α-Aziridinyl Carbenium Ion Intermediate and Stereoselective Dehydroxylative Diarylation of Aziridin-2-yl Carboxaldehyde

被引：3
|
作者：
Ranjith, Jala [1 ]
Jeong, Yeolib [2 ]
Kim, Hyunwoo [2 ]
Ha, Hyun-Joon [1 ]
机构：
[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, South Korea
[2] Korea Adv Inst Sci & Technol KAIST, Dept Chem, Daejeon 34141, South Korea
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 07期
基金：
新加坡国家研究基金会;
关键词：
Aziridines; Carbenium ion; Density functional calculations; Lewis acids; Stereoselective arylation; FRIEDEL-CRAFTS ALKYLATION; NUCLEOPHILIC-SUBSTITUTION; STABLE CARBOCATIONS; EFFICIENT SYNTHESIS; BENZYLIC ARYLATION; AMINO-ALCOHOLS; CHEMISTRY; ANNULATION; AMINATION; TERTIARY;
D O I：
10.1002/ajoc.202200186
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha-Aziridinyl carbenium ion as an intermediate was observed for the first time from the reaction of aziridin-2-yl arylmethanol with Lewis acid BF3 center dot OEt2. This intermediate was further reacted with various nucleophiles including electron-rich arenes to afford the adducts in highly stereoselective manner as singly isomers. alpha-Aziridinyl carbenium ion intermediate was observed spectroscopically as a crucial intermediate, and density functional theory (DFT) calculations show the origin of stereoselectivity based on thermodynamic preference for the reaction.
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页数：7
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