Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO

被引：36

作者：

Vatele, Jean-Michel ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5246, ICBMS,Lab Chim Organ 1, F-69622 Villeurbanne, France

来源：

TETRAHEDRON | 2010年 / 66卷 / 04期

关键词：

Copper(II) salts; Iodosylbenzene; Oxidation; Rearrangement; TEMPO; DIRECT STEREOSELECTIVE SYNTHESES; SELECTIVE AEROBIC OXIDATION; 1,3-OXIDATIVE REARRANGEMENTS; REAGENTS; TRANSPOSITION; ALDEHYDES; ADDITIONS; KETONES; ENONES; CONSTRUCTION;

D O I：

10.1016/j.tet.2009.11.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two methods for the oxidative rearrangement of tertiary allylic alcohols have been developed. Most of tertiary allylic alcohols studied were oxidized to their corresponding transposed carbonyl derivatives in excellent to fair yields by reaction with TEMPO in combination with PhIO and Bi(OTf)(3) or copper (II) chloride in the presence or not of oxygen. Other primary oxidants of TEMPO such as PhI(OAc)(2), mCPBA, and Oxone (R) were unsatisfactory giving the enone in modest to low yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：904 / 912

页数：9

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