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

页码：2925 / 2928

页数：4

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