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

页码：3249 / 3253

页数：5

共 50 条

[31] Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines
Chen, Xiang-Yu
Lin, Ruo-Chen
Ye, Song
CHEMICAL COMMUNICATIONS, 2012, 48 (09) : 1317 - 1319
[32] An efficient [4+3] cycloaddition reaction of aza-o-quinodimethanes with C,N-cyclic azomethine imines: stereoselective synthesis of 1,2,4-triazepines
Chen, L.
Yang, G. M.
Wang, J.
Jia, Q. F.
Wei, J.
Du, Z. Y.
RSC ADVANCES, 2015, 5 (94): : 76696 - 76699
[33] Divergent transformation of C,N-cyclic-N'-acyl azomethine imines by reaction with diazo compounds
Ohno, Haruki
Takahashi, Ryosuke
Suga, Takuya
Soeta, Takahiro
Ukaji, Yutaka
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (39) : 7891 - 7894
[34] A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triaze-pines
Wang, Xinyue
Li, Zefei
Feng, Chang
Zhen, Qi
Guo, Mingzhang
Hou, Yunlei
Gong, Ping
SYNLETT, 2021, 32 (20) : 2090 - 2096
[35] Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines
Pozgan, Franc
Al Mamari, Hamad
Groselj, Uros
Svete, Jurij
Stefane, Bogdan
MOLECULES, 2018, 23 (01):
[36] Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines
Chakrabarty, Shyamal
Chatterjee, Indranil
Wibbeling, Birgit
Daniliuc, Constantin Gabriel
Studer, Armido
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) : 5964 - 5968
[37] 1,3-Dipolar cycloaddition of isatinN,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water
Wang, Zhan-Yong
Yang, Ting
Chen, Rongxiang
Ma, Xueji
Liu, Huan
Wang, Kai-Kai
RSC ADVANCES, 2020, 10 (41) : 24288 - 24292
[38] Phosphine-Catalyzed Diastereoselective [3+3] Annulation of Morita-Baylis-Hillman Carbonates with C,N-Cyclic Azomethine Imines
Zhang, Lei
Yang, Wenjun
Zhou, Leijie
Liu, Honglei
Huang, Jiaxing
Xiao, Yumei
Guo, Hongchao
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3377 - 3388
[39] Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids
Kowalska, Ewelina
Sieron, Leslaw
Albrecht, Anna
MOLECULES, 2022, 27 (20):
[40] Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral γ-Lactams
Espinosa, Miguel
Blay, Gonzalo
Cardona, Luz
Carmen Munoz, M.
Pedro, Jose R.
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (59) : 14707 - 14711

← 1 2 3 4 5 →