Stereospecific Synthesis of 2-Iminothiazolidines via Domino Ring-Opening Cyclization of Activated Aziridines with Aryl- and Alkyl Isothiocyanates

被引：41
|
作者：
Bhattacharyya, Aditya [1 ]
Kavitha, C. V. [2 ]
Ghorai, Manas K. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] Govt Coll Women, Dept Chem, Mandya 571401, Karnataka, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期
关键词：
DONOR-ACCEPTOR CYCLOPROPANES; MEDIATED 3+2 CYCLOADDITIONS; CATALYZED CYCLOADDITION; BOND FORMATION; HETEROCUMULENES; DERIVATIVES; MALONONITRILE; DROC; MICE;
D O I：
10.1021/acs.joc.6b01551
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid catalyzed domino ring-opening cyclization of activated aziridines with aryl and alkyl isothiocyanates has been accomplished leading to the formation of a wide variety of highly substituted and functionalized 2-iminothiazolidines with excellent diastereo- and enantiospecificity (de, ee up to >99%). The reaction proceeds via a Lewis acid catalyzed S(N)2-type ring opening of the activated aziridine followed by a concomitant 5-exo-dig cyclization in a domino fashion to furnish the 2-iminothiazolidine derivative in excellent yields (up to 99%).
引用
收藏
页码：6433 / 6443
页数：11
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