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
收藏
页码：5234 / 5240
页数：7
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