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.
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页码：5234 / 5240
页数：7
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