A NEW VERSATILE FLUORINATED-C(4) CHIRON

被引:17
作者
ARNONE, A
BRAVO, P
CAVICCHIO, G
FRIGERIO, M
MARCHETTI, V
VIANI, F
ZAPPALA, C
机构
[1] POLITECN MILAN,CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM,I-20133 MILAN,ITALY
[2] UNIV LAQUILA,DIPARTIMENTO GASTROENTEROL,I-67100 LAQUILA,ITALY
关键词
D O I
10.1016/S0040-4039(00)61160-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically pure 2-(fluoromethyl)-2-[(4-methylphenylsulphinyl)methyl]oxirane has been obtained in good yield and with high d.e. by reacting diazomethane with optically pure 1-fluoro-3-(4-methylphenylsulphinyl)propan-2-one. Regio- and stereo-selective openings of oxirane ring performed with selected nucleophiles afforded several useful derivatives.
引用
收藏
页码:5609 / 5612
页数:4
相关论文
共 28 条
  • [1] BRAVO P, 1990, GAZZ CHIM ITAL, V120, P275
  • [2] BRAVO P, 1988, SYNTHESIS-STUTTGART, P955
  • [3] BRAVO P, 1986, SYNTHESIS-STUTTGART, P579
  • [4] PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS
    BRAVO, P
    RESNATI, G
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (10) : 661 - 692
  • [5] AN EFFICIENT APPROACH TO ENANTIOMERICALLY PURE FLUORHYDRINS
    BRAVO, P
    RESNATI, G
    [J]. TETRAHEDRON LETTERS, 1987, 28 (41) : 4865 - 4866
  • [6] SYNTHESIS OF 4 HOMOCHIRAL 3,4-DIDEOXY-3-FLUORO-HEXOSES FROM A NONCARBOHYDRATE PRECURSOR
    BRAVO, P
    FRIGERIO, M
    FRONZA, G
    IANNI, A
    RESNATI, G
    [J]. TETRAHEDRON, 1990, 46 (03) : 997 - 1008
  • [7] ASYMMETRIC-SYNTHESIS AND STRUCTURAL-ANALYSIS OF 5-O-BENZOYL-2,3-DIDEOXY-3-FLUORO-ALPHA,BETA-D-RIBOFURANOSE AND 5-O-BENZOYL-2,3-DIDEOXY-3-FLUORO-ALPHA,BETA-D-XYLOFURANOSE FROM HOMOCHIRAL 1-FLUORO-3-SULFINYLACETONE
    BRAVO, P
    PIOVOSI, E
    RESNATI, G
    FRONZA, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) : 5171 - 5176
  • [8] A NEW ENTRY TO HOMOCHIRAL DIFLUORINATED COMPOUNDS
    BRAVO, P
    PREGNOLATO, M
    RESNATI, G
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (11) : 1105 - 1106
  • [9] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES
    CARRENO, MC
    RUANO, JLG
    MARTIN, AM
    PEDREGAL, C
    RODRIGUEZ, JH
    RUBIO, A
    SANCHEZ, J
    SOLLADIE, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) : 2120 - 2128
  • [10] EFFICIENT METAL SALT CATALYZED AZIDOLYSIS OF EPOXIDES WITH SODIUM-AZIDE IN ACETONITRILE
    CHINI, M
    CROTTI, P
    MACCHIA, F
    [J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5641 - 5644