RHODIUM-MEDIATED INSERTION OF CF3-SUBSTITUTED CARBENOID INTO O-H - AN EFFICIENT METHOD FOR THE SYNTHESIS OF ALPHA-TRIFLUOROMETHYLATED ALKOXYACETIC AND ARYLOXYACETIC ACID-DERIVATIVES

被引:49
作者
SHI, GQ
CAO, ZY
CAI, WL
机构
[1] Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Academia Sinica, 200032 Shanghai
关键词
D O I
10.1016/0040-4020(95)98698-H
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CF3-substituted diazo compound 2 undergoes a facile rhodium carbenoid mediated O-H insertion reaction with a variety of alcohols and phenols to afford the title compounds in good yield. Use of the title compounds as synthetic precursors for other fluorinated molecules is exemplified by the transformation of the product 3b, into beta, beta-difluoro-alpha-ketoester 5 and alpha-hydroxyketone 8.
引用
收藏
页码:5011 / 5018
页数:8
相关论文
共 33 条
  • [1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS
    ADAMS, J
    SPERO, DM
    [J]. TETRAHEDRON, 1991, 47 (10-11) : 1765 - 1808
  • [2] DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF HOMOCHIRAL ALCOHOLS
    ALLER, E
    COX, GG
    MILLER, DJ
    MOODY, CJ
    [J]. TETRAHEDRON LETTERS, 1994, 35 (32) : 5949 - 5952
  • [3] [3,3]-SIGMATROPIC REARRANGEMENTS OF FLUOROCARBANIONS
    ANDREEV, VG
    KOLOMIETS, AF
    FOKIN, AV
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (03) : 259 - 269
  • [4] [Anonymous], 1993, ORGANOFLUORINE COMPO
  • [5] BRUNNER H, 1992, ANGEW CHEM INT EDIT, V31, P1183, DOI 10.1002/anie.199211831
  • [6] COMPETING O-H INSERTION AND BETA-ELIMINATION IN RHODIUM CARBENOID REACTIONS - SYNTHESIS OF 2-ALKOXY-3-ARYLPROPANOATES
    COX, GG
    HAIGH, D
    HINDLEY, RM
    MILLER, DJ
    MOODY, CJ
    [J]. TETRAHEDRON LETTERS, 1994, 35 (19) : 3139 - 3142
  • [7] RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST
    COX, GG
    MILLER, DJ
    MOODY, CJ
    SIE, ERHB
    KULAGOWSKI, JJ
    [J]. TETRAHEDRON, 1994, 50 (10) : 3195 - 3212
  • [8] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
    DOYLE, MP
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
  • [9] Filler R., 1982, BIOMEDICAL ASPECTS F
  • [10] FRAZEN V, 1957, LIEBIGS ANN CHEM, V602, P199