Electronically promoted payne rearrangement of 3-CF3-2,3-epoxyalcohols

被引:21
作者
Yamazaki, T [1 ]
Ichige, T [1 ]
Kitazume, T [1 ]
机构
[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
D O I
10.1021/ol048229x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF3 group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.
引用
收藏
页码:4073 / 4076
页数:4
相关论文
共 14 条
[1]   Julia-Colonna asymmetric epoxidation reactions under non-aqueous conditions: Rapid, highly regio- and stereo-selective transformations using a cheap, recyclable catalyst [J].
Allen, JV ;
Bergeron, S ;
Griffiths, MJ ;
Mukherjee, S ;
Roberts, SM ;
Williamson, NM ;
Wu, LE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3171-3179
[2]   ARYL TRIFLUOROMETHYL KETONE HYDRATES AS PRECURSORS OF CARBOXYLIC-ACIDS AND ESTERS [J].
DELGADO, A ;
CLARDY, J .
TETRAHEDRON LETTERS, 1992, 33 (20) :2789-2790
[3]  
FRISCH MJ, 2003, COMPUTATION CARRIED
[4]   First highly diastereoselective synthesis of syn α-methyl β-fluoroalkyl β-amino esters [J].
Fustero, S ;
Pina, B ;
de la Torre, MG ;
Navarro, A ;
de Arellano, CR ;
Simón, A .
ORGANIC LETTERS, 1999, 1 (07) :977-980
[5]  
Hanson, 2002, ORG REACTIONS, V60, P1
[6]  
Malek J., 1985, Org. React, V34, P1
[7]   INVERSION OF CONFIGURATIONS OF CONTIGUOUS CARBINOL CENTERS - APPLICATION TO THE SYNTHESIS OF BOTH ENANTIOMERS OF NATURAL-PRODUCTS FROM THE SAME ENANTIOMERICALLY PURE STARTING MATERIAL [J].
PRASIT, P ;
ROBERTSON, G ;
ROKACH, J .
CARBOHYDRATE RESEARCH, 1990, 202 :93-104
[8]   ANALYSIS OF 2 C-13 NMR CORRELATIONS FOR DETERMINING THE STEREOCHEMISTRY OF 1,3-DIOL ACETONIDES [J].
RYCHNOVSKY, SD ;
ROGERS, B ;
YANG, G .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3511-3515
[9]   STEREOSELECTIVE SYNTHESIS OF TRIFLUOROMETHYLATED COMPOUNDS WITH CONTROLLED ADJACENT TERTIARY CARBONS BY MICHAEL ADDITION TO (E)-3-(TRIFLUOROMETHYL)ACRYLATES [J].
SHINOHARA, N ;
HAGA, J ;
YAMAZAKI, T ;
KITAZUME, T ;
NAKAMURA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4363-4374
[10]  
Von dem Bussche-Hunnefeld C., 1992, CHEM BER, V125, P1273