Auxiliary-Enabled Pd-Catalyzed Direct Arylation of Methylene C(sp3)-H Bond of Cyclopropanes: Highly Diastereoselective Assembling of Di- and Trisubstituted Cyclopropanecarboxamides

被引：86

作者：

Parella, Ramarao ^{[1
]}

Gopalakrishnan, Bojan ^{[1
]}

Babu, Srinivasarao Arulananda ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Mohali, Punjab, India

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 13期

关键词：

CONFORMATIONAL RESTRICTION APPROACH; C-H ARYLATION; ORGANIC-SYNTHESIS; ASYMMETRIC CYCLOPROPANATION; PALLADIUM; FUNCTIONALIZATION; ACTIVATION; RING; STRATEGY; ACCESS;

D O I：

10.1021/ol4012212

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An auxiliary-enabled and Pd(OAc)(2)-catalyzed direct arylation of C(sp(3))-H bonds of cyclopropanes and production of di- and trisubstituted cyclopropanecarboxamides having contiguous stereocenters are reported. The installation of aryl groups on cyclopropanecarboxamides led to the assembling of novel mono- and di- aryl-N-(quinolin-8-yl)cyclopropanecarboxamide scaffolds and mono- and di- aryl-N-(2-(methylthio)phenyl)cyclopropanecarboxamides. The stereochemistry of products was unequivocally assigned from the X-ray structures of key compounds.

引用

页码：3238 / 3241

页数：4

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