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
收藏
页码：1515 / 1518
页数：4
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