A conjugate addition sulfoxide elimination route to allylic difluorophosphonates

被引:23
作者
Blades, K [1 ]
Percy, JM [1 ]
机构
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(98)02000-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluoromethynithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sulfoxide elimination afforded the products of formal vinylation, attaching the difluoromethylenephosphonato group to an alkenyl carbon atom. With acyclic vinyl sulfoxides, the addition occurred in moderate to poor yield. Addition failed completely in the absence of cerium(III) chloride, and was facilitated by an excess of the reagent. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9085 / 9088
页数:4
相关论文
共 13 条
  • [1] A reproducible and high-yielding cerium-mediated route to alpha,alpha-difluoro-beta-ketophosphonates.
    Blades, K
    Lequeux, TP
    Percy, JM
    [J]. TETRAHEDRON, 1997, 53 (30) : 10623 - 10632
  • [2] Conjugate addition reactions of a (diethoxyphosphinoyl)difluoromethyl anion equivalent to acyclic and cyclic vinyl sulfones.
    Blades, K
    Lapotre, D
    Percy, JM
    [J]. TETRAHEDRON LETTERS, 1997, 38 (33) : 5895 - 5898
  • [3] Fluorinated ylides and related compounds
    Burton, DJ
    Yang, ZY
    Qiu, WM
    [J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1641 - 1715
  • [4] Free radical chain reactions for the preparation of novel anomeric carbohydrate difluoromethylene-phosphonates and -phosphonothioates.
    Herpin, TF
    Motherwell, WB
    Roberts, BP
    Roland, S
    Weibel, JM
    [J]. TETRAHEDRON, 1997, 53 (44) : 15085 - 15100
  • [5] CHLOROSULFENYLATION-DEHYDROCHLORINATION REACTIONS - NEW AND IMPROVED METHODOLOGY FOR SYNTHESIS OF UNSATURATED ARYL SULFIDES AND ARYL SULFONES
    HOPKINS, PB
    FUCHS, PL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) : 1208 - 1217
  • [6] Lee AWM, 1997, TOP CURR CHEM, V190, P103
  • [7] Li AR, 1996, SYNTHESIS-STUTTGART, P606
  • [8] Percy JM, 1997, TOP CURR CHEM, V193, P131
  • [9] PERLMUTTER P, 1992, CONJUGATE ADDITION R, P170
  • [10] A facile solution and solid phase synthesis of phosphotyrosine mimetic L-4-[diethylphosphono(difluoromethyl)]-phenylalanine (F(2)Pmp(EtO)(2)) derivatives
    Qabar, MN
    Urban, J
    Kahn, M
    [J]. TETRAHEDRON, 1997, 53 (32) : 11171 - 11178