Radical Acylation of [1.1.1]Propellane with Aldehydes: Synthesis of Bicyclo[1.1.1]pentane Ketones

被引：13

作者：

Li, Qing ^{[1
]}

Li, Lin ^{[1
]}

Xu, Qiao-Ling ^{[1
]}

Pan, Fei ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 23期

基金：

中国国家自然科学基金;

关键词：

STRAIN-RELEASE; DESIGN; SCOPE;

D O I：

10.1021/acs.orglett.2c01707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclo[1.1.1]pentanes (BCPs) are widely utilized in drug design as sp(3)-rich bioisosteres for tert-butyl, internal alkynes, and aryl groups. A general and mild method for radical acylation of [1.1.1]propellane with aldehydes has been developed. The protocol provides straightforward access to bicyclo[1.1.1]pentane ketones with a broad substrate scope. The synthetic utility of this methodology is demonstrated by the late-stage modification of bioactive molecules and the versatile transformation of bicyclo[1.1.1]pentane ketones, making it useful for drug discovery.

引用

页码：4292 / 4297

页数：6

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