1,3-diol synthesis via controlled, radical-mediated C-H functionalization

被引：186

作者：

Chen, Ke ^{[1
]}

Richter, Jeremy M. ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 23期

基金：

美国国家航空航天局;

关键词：

D O I：

10.1021/ja802491q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radicalmediated C-H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann-Loffler-Freytag reaction, cyclization, and hydrolysis to provide the 1,3-diols. In addition to the 10 examples presented herein, the syntheses of four natural products are facilitated by this directed oxyfunctionalization. This methodology is demonstrated to be orthogonal to other known C-H oxidations. Finally, this sequence is efficient, practical, inexpensive, and scalable.

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页码：7247 / +

页数：4

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