Ring opening of DA-cyclopropanes with electron rich arene/heteroarene: synthesis of 2-(2,2-diarylethyl)malonates

被引：26

作者：

Talukdar, Ranadeep ^{[1
]}

Saha, Amrita ^{[1
]}

Tiwari, Deo Prakash ^{[1
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON | 2016年 / 72卷 / 05期

关键词：

2-(2,2-Diarylethyl)malonates; DA-cyclopropanes; Nucleophilic ring opening; Electron rich arena; Indole; DONOR-ACCEPTOR CYCLOPROPANES; ACID-CATALYZED-REACTIONS; ASYMMETRIC-SYNTHESIS; CYCLOADDITIONS; DERIVATIVES; LACTONES; ROUTE;

D O I：

10.1016/j.tet.2015.12.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient strategy for nucleophilic ring opening of donor-acceptor (DA)-cyclopropanes with electron rich arenes to provide 2-(2,2-diarylethyl)malonates in excellent yields is described. The reaction was found to be successful with heteroarenes as the nucleophile as well. Reaction of enantiopure DA-cyclopropane with arene/heteroarene as the nucleophiles afforded the corresponding 2-(2,2-diarylethyl)malonates with high yield and enantioselectivity (ee 95%). The synthetic utility of the products was demonstrated by converting them easily into other important synthetic scaffolds like functionalized cyclohexene and malonic acid derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：613 / 624

页数：12

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