An efficient, one-pot, three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

被引：31

作者：

Salahi, Farbod ^{[1
]}

Taghizadeh, Mohammad Javad ^{[1
,2
]}

Arvinnezhad, Hamid ^{[1
]}

Moemeni, Mehdi ^{[1
]}

Jadidi, Khosrow ^{[1
]}

Notash, Behrouz ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Dept Chem, Gc Tehran 1983963113, Iran

[2] Imam Hossein Univ, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 09期

关键词：

Catalytic asymmetric multicomponent; reaction; Asymmetric 1,3-dipolar cycloaddition; Cyclohexane-1,2-bis(arylmethyleneamine); Azomethine ylide; Chiral spirooxindolopyrrolizidines; STRUCTURE-BASED DESIGN; AZOMETHINE YLIDES; PYRROLIZIDINE ALKALOIDS; EPOXIDATION; ACTIVATION; EPOXIDES; CHLORIDE; PLANTS;

D O I：

10.1016/j.tetlet.2013.11.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic, highly regio-, diastereo-, and enantioselective synthesis of a small library of chiral spirooxindolopyrrolizidines via a three-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophiles, 3-(2-alkenoy1)-1,3-oxazolidin-2-ones, is described. A chiral copper(II) complex of cyclohexane-1,2-bis(arylmethyleneamine) catalyzed this process at room temperature. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1515 / 1518

页数：4

共 50 条

[41] An Efficient One-Pot Synthesis of Dispiropyrrolidine Derivatives Through 1,3-Dipolar Cycloaddition Reactions Under Ultrasound Irradiation
Liu, Hai
Zou, Yi
Hu, Yu
Shi, Da-Qing
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (04) : 877 - 881
[42] Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral bronsted acid activated dipole
Chen, Xiao-Hua
Zhang, Wen-Quan
Gong, Liu-Zhu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5652 - +
[43] A novel one-pot, three-component access to hexahydropyrrolo[2,1-a]isoquinolines by an alkylation-dehydrohalogenation-1,3-dipolar cycloaddition sequence
Nyerges, M
Somfai, B
Tóth, J
Töke, L
Dancsó, A
Blaskó, G
SYNTHESIS-STUTTGART, 2005, (12): : 2039 - 2045
[44] Highly efficient one-pot, three-component synthesis of 1,5-benzodiazepine derivatives
Li, Xiao-Qing
Wang, Lan-Zhi
CHINESE CHEMICAL LETTERS, 2014, 25 (02) : 327 - 332
[45] Three-component one-pot synthesis of new spiro[indoline-pyrrolidine] derivatives mediated by 1,3-dipolar reaction and DFT analysis
Yazmin Villarreal
Braulio Insuasty
Rodrigo Abonia
Alejandro Ortiz
Pablo Romo
Jairo Quiroga
Monatshefte für Chemie - Chemical Monthly, 2021, 152 : 497 - 506
[46] FACILE THREE-COMPONENT SYNTHESIS OF SPIROOXINDOLEPYRROLOLINE RING SYSTEMS VIA 1,3-DIPOLAR CYCLOADDITION WITH 1,4-NAPHTHOQUINONE
Chen, Hua
Wang, Shun-Yi
Xu, Xiao-Ping
Ji, Shun-Jun
SYNTHETIC COMMUNICATIONS, 2011, 41 (22) : 3280 - 3288
[47] Efficient synthesis of novel imidazo[1,2-a]pyrimidine derivatives via one-pot three-component procedure
Sadjadi, Samahe
Nahavandi, Fatemeh
Heravi, Majid M.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (06) : 1049 - 1052
[48] One-pot three-component catalytic asymmetric synthesis of homoallylboronates
Ibrahem, Ismail
Afewerki, Samson
Breistein, Palle
Cordova, Armando
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[49] Three-component one-pot synthesis of new spiro[indoline-pyrrolidine] derivatives mediated by 1,3-dipolar reaction and DFT analysis
Villarreal, Yazmin
Insuasty, Braulio
Abonia, Rodrigo
Ortiz, Alejandro
Romo, Pablo
Quiroga, Jairo
MONATSHEFTE FUR CHEMIE, 2021, 152 (05): : 497 - 506
[50] Efficient synthesis of novel imidazo[1,2-a]pyrimidine derivatives via one-pot three-component procedure
Samahe Sadjadi
Fatemeh Nahavandi
Majid Heravi
Journal of the Iranian Chemical Society, 2015, 12 : 1049 - 1052

← 1 2 3 4 5 →