Highly Diastereoselective Preparation of Tertiary Alkyl Isonitriles by Stereoinvertive Nucleophilic Substitution at a Nonclassical Carbocation

被引：8

作者：

Chen, Xu ^{[1
,2
]}

Marek, Ilan ^{[1
,2
]}

机构：

[1] Technion Israel Inst Technol, Schulich Fac Chem, IL-3200009 Haifa, Israel

[2] Technion Israel Inst Technol, Resnick Sustainabil Ctr Catalysis, IL-3200009 Haifa, Israel

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 13期

基金：

以色列科学基金会;

关键词：

MULTICOMPONENT REACTIONS; ISOCYANIDE INSERTION; CATALYZED REACTIONS; DIRECT CONVERSION; ALCOHOLS; CONSTRUCTION; STEREOCENTERS;

D O I：

10.1021/acs.orglett.3c00583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient SnCl4-catalyzed nucleophilic isocyanation of cyclopropyl ethers has been developed. The reaction proceeds at the quaternary carbon stereocenter of the cyclopropane with a complete inversion of configuration, providing a new avenue for the construction of synthetically challenging tertiary alkyl isonitriles with high diastereopurity. The diversity of the incorporated isocyanide group has been demonstrated by the transformation of tertiary alkyl isonitriles into the corresponding tertiary alkyl amines, amides, and cyclic ketoimines.

引用

页码：2285 / 2288

页数：4

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