Rh(II)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides

被引：31

作者：

Li, Yuye ^{[1
,2
,3
]}

Huang, Zhongxing ^{[2
,3
]}

Wu, Xinhu ^{[1
,2
,3
]}

Xu, Peng-Fei ^{[1
]}

Jin, Jing ^{[1
]}

Zhang, Yan ^{[1
,2
,3
]}

Wang, Jianbo ^{[2
,3
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Peking Univ, BNLMS, Coll Chem, Minist Educ, Beijing 100871, Peoples R China

[3] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Coll Chem, Minist Educ, Beijing 100871, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 26期

关键词：

2,3]-Sigmatropic rearrangement; Sulfur ylides; N-Tosylhydrazone; Allylic phenyl sulfides; Propargyl phenyl sulfides; CROSS-COUPLING REACTIONS; DIAZO-COMPOUNDS; ORGANIC-SYNTHESIS; <2,3>-SIGMATROPIC REARRANGEMENT; CARBONYL-COMPOUNDS; CATALYTIC METHODS; EPOXY SULFONE; GAMMA-EPOXY; CARBENOIDS; CYCLIZATION;

D O I：

10.1016/j.tet.2012.03.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, Rh-2(OAc)(4)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides is reported. A series of tosylhydrazones derived from aldehydes were successfully used for [2,3]-sigmatropic rearrangement by reaction with either allylic phenyl sulfides or propargyl phenyl sulfides. The reaction conditions were optimized and afforded the products in moderate to good yields. In addition, a novel and convenient approach for the synthesis of cyclobutenones and cyclopropanes has been developed through direct oxidation of the rearrangement products. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5234 / 5240

页数：7

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