From Propargylic Amides to Functionalized Oxazoles: Domino Gold Catalysis/Oxidation by Dioxygen

被引：145

作者：

Hashmi, A. Stephen K. ^{[1
]}

Jaimes, Maria Camila Blanco ^{[1
]}

Schuster, Andreas M. ^{[1
]}

Rominger, Frank ^{[1
]}

机构：

[1] Univ Heidelberg, Organ Chem Inst, D-69120 Heidelberg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 15期

关键词：

2,5-DISUBSTITUTED OXAZOLES; RADICAL POLYMERIZATION; CATALYZED CYCLIZATION; HOMOGENEOUS CATALYSIS; CLEAVAGE REACTIONS; ANTIOXIDANT; DERIVATIVES; OXIDATION; CYCLOISOMERIZATION; METABOLITES;

D O I：

10.1021/jo301288w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.

引用

页码：6394 / 6408

页数：15

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