Stereospecific [3+2] Cycloaddition of Chiral Arylallenes with C,N- Cyclic Azomethine Imines

被引：1
作者：
Liu, Xinyu [1 ]
Liu, Zhixin [1 ]
Hu, Yongyi [3 ]
Huang, Kuo-Wei [3 ,4 ,5 ]
Ajitha, Manjaly J. [3 ]
Wang, De [1 ,2 ]
机构：
[1] Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, Qingdao 266100, Peoples R China
[2] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
[3] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Phys Sci & Engn Div, Thuwal 239556900, Saudi Arabia
[4] Agcy Sci Technol & Res, Inst Mat Res & Engn, Singapore 138634, Singapore
[5] Inst Sustainabil Chem Energy & Environm, Singapore 138634, Singapore
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 18期
关键词：
1,3-DIPOLAR CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALLENES; CHEMISTRY;
D O I：
10.1021/acs.orglett.3c00984
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel alpha,beta-regioselective [3+2] cycloaddition reaction of arylallene with C,N-cyclic azomethine imine is reported. The axial-to-central chirality transfer phenomenon has been disclosed with chiral allenes in the reaction. The wide substrate scope, including different functional groups and natural products, reveals the generality of the methodology. Both experiments and density functional theory calculations have been used to elucidate a plausible mechanism.
引用
收藏
页码：3249 / 3253
页数：5
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