Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides

被引：45
|
作者：
Bhattacharyya, Aditya [1 ]
Shahi, Chandan Kumar [1 ]
Pradhan, Sajan [1 ]
Ghorai, Manas K. [1 ]
机构：
[1] Indian Inst Technol Kanpur, Kanpur 208016, Uttar Pradesh, India
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 10期
关键词：
DERIVATIVES TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; TOSYLMETHYL ISOCYANIDE; ABSOLUTE STRUCTURE; FORMAL 3+2; CYCLOADDITION; INDOLES; 2-ARYL-N-TOSYLAZETIDINES; HETEROCYCLIZATION; 2-ARYLAZIRIDINES;
D O I：
10.1021/acs.orglett.8b00986
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An expeditious synthetic route to access structurally diverse 1,4,5,6-tetrahydropyrimidines via domino ring-opening cyclization of activated aziridines with alpha-acidic isocyanides has been established. The transformation proceeds via Lewis acid mediated S-N(2)-type ring opening of activated aziridines with alpha-carbanion of the isocyanides followed by a concomitant 6-endo-dig cyclization in a domino fashion to furnish the 1,4,5,6-tetrahydropyrimidine derivatives in excellent yields (up to 84%) and also in diastereo- and enantiomerically pure form (dr > 99:1, ee > 99%).
引用
收藏
页码：2925 / 2928
页数：4
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