α-Sulfinyl carbanions as a new source of olefins

被引:23
作者
Abramovitch, A [1 ]
Varghese, JP
Marek, I
机构
[1] Technion Israel Inst Technol, Dept Chem, IL-32000 Haifa, Israel
[2] Technion Israel Inst Technol, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel
关键词
D O I
10.1021/ol036450o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Secondary alpha-lithiosulfinyl carbanions react either intermolecularly, after transmetalation into an organocopper derivative in an S(N)2-type process with zinc carbenoid, or intramolecularly via higher-order zincate to give, through a tandem zinc homologation-beta-elimination reaction the corresponding alkenes. alpha,alpha-Disubstituted alkenes are only formed from tertiary alpha-lithiosulfinyl carbanions via the 1,2-metalate rearrangement.
引用
收藏
页码:621 / 623
页数:3
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共 43 条
  • [1] Lithiated beta-aminoalkyl sulfones as mono and dinucleophiles in the preparation of nitrogen heterocycles: Application to the synthesis of capsazepine
    Alonso, DA
    Costa, A
    Mancheno, B
    Najera, C
    [J]. TETRAHEDRON, 1997, 53 (13) : 4791 - 4814
  • [2] Lithiated gamma-tosyl-substituted benzylmethallylamine: New gamma-amino methallyl sulfone anions in organic synthesis
    Alonso, DA
    Falvello, LR
    Mancheno, B
    Najera, C
    Tomas, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) : 5004 - 5012
  • [3] alpha-nitrogenated organolithium compounds from alpha-amidomethyl and alpha-aminomethyl sulfones
    Alonso, DA
    Alonso, E
    Najera, C
    Ramon, DJ
    Yus, M
    [J]. TETRAHEDRON, 1997, 53 (13) : 4835 - 4856
  • [4] A new approach towards the synthesis of sp3 1,1-diiodoalkanes
    Aufauvre, L
    Knochel, P
    Marek, I
    [J]. CHEMICAL COMMUNICATIONS, 1999, (21) : 2207 - 2208
  • [5] THE COPPER(I)-CATALYZED COUPLING OF GRIGNARD-REAGENTS WITH 5-LITHIO-2,3-DIHYDROFURAN AND 6-LITHIO-3,4-DIHYDRO-2H-PYRAN
    BARBER, C
    BURY, P
    KOCIENSKI, P
    OSHEA, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) : 1595 - 1597
  • [6] Preparation, solid-state structure, and synthetic applications of isolable and storable haloalkylzinc reagents
    Charette, AB
    Marcoux, JF
    Molinaro, C
    Beauchemin, A
    Brochu, C
    Isabel, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) : 4508 - 4509
  • [7] Diastereo- and enantioselective synthesis of 1,2,3-substituted cyclopropanes with zinc carbenoids
    Charette, AB
    Lemay, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10): : 1090 - 1092
  • [8] A CONVENIENT PREPARATION OF MONO-DI-HALOGENOALKENES OR GEM-DI-HALOGENOALKENES FROM ALPHA-SULFONYL CARBANIONS AND HALOGENOLITHIOCARBENOIDS
    CHARREAU, P
    JULIA, M
    VERPEAUX, JN
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 379 (03) : 201 - 210
  • [9] CHEMLA F, 1993, SYNLETT, P665
  • [10] TOTAL SYNTHESIS OF MAYTANSINE
    COREY, EJ
    WEIGEL, LO
    CHAMBERLIN, AR
    CHO, H
    HUA, DH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) : 6613 - 6615