π-Deficient α-arylsulfonyl esters as soft nucleophiles in organic synthesis

被引:9
作者
Alonso, DA [1 ]
Nájera, C [1 ]
Varea, M [1 ]
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
关键词
sulfones; PTC; aconitate; dialkylation;
D O I
10.1016/S0040-4039(01)01920-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Different pi -deficient arylsulfonyl groups have been studied as candidates for the stabilization of a-sulfonyl esters. The 3,5-bis(trifluoromethyl)phenylsulfonyl group has been shown to be the best substituent for the stereoselective synthesis of E-aconitates by a dialkylation-dehydrosulfinylation integrated process under PTC conditions using K2CO3 as base. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8845 / 8848
页数:4
相关论文
共 20 条
  • [1] Observations on the alkylation of β-acetalic carbanions:: Monoalkylation versus dialkylation and elimination
    Ballini, R
    Bosica, G
    Cossu, S
    De Lucchi, O
    Peluso, P
    [J]. TETRAHEDRON, 2001, 57 (20) : 4461 - 4465
  • [2] BLANEY JJ, 1998, TETRAHEDRON, V54, P14989
  • [3] Effect of aryl substituents on rate of desulfonylation of aryl alkyl sulfones:: Superiority of p-fluorophenyl- and 2-naphthyl sulfones
    Clive, DLJ
    Yeh, VSC
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (18) : 3267 - 3274
  • [4] IMPROVED SYNTHESIS OF TRIFLUOROMETHYL SULFONES USED AS INTERMEDIATES FOR THE PREPARATION OF DISUBSTITUTED OR TRI-SUBSTITUTED OLEFINS
    EUGENE, F
    LANGLOIS, B
    LAURENT, E
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (03) : 301 - 309
  • [5] Goumont R, 1999, EUR J ORG CHEM, V1999, P2969
  • [6] Gurnani J, 1999, HUNG J IND CHEM, V27, P1
  • [7] A MILD METHOD FOR THE REDUCTIVE DESULFURIZATION OF ALPHA-PHENYLTHIO AND ALPHA-PHENYLSULFINYL CARBONYL-COMPOUNDS
    HOLTON, RA
    CROUSE, DJ
    WILLIAMS, AD
    KENNEDY, RM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) : 2317 - 2318
  • [8] JIN Z, 1999, PHOSPHORUS SULFUR, V95, P1
  • [9] Desulfonylation reactions:: Recent developments
    Nájera, C
    Yus, M
    [J]. TETRAHEDRON, 1999, 55 (35) : 10547 - 10658
  • [10] Nájera C, 1998, RRD ORG CHEM, V2, P637