Aryl-substituted sulfonium betaines: Preparation and use in the epoxidation of aldehydes

被引:11
作者
Forbes, David C. [1 ]
Amin, Sejal R.
Bean, Christie J.
Standen, Michael C.
机构
[1] Univ S Alabama, Dept Chem, Mobile, AL 36688 USA
[2] Synthetech, Albany, OR 97321 USA
关键词
D O I
10.1021/jo061370u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermally induced decarboxylation of carboxymethylsulfonium betaines results in formation of the corresponding sulfur ylides in situ. Decarboxylation rates for a range of arylcarboxymethylsulfonium betaine salts have been determined using NMR spectroscopy, and the efficiency of ylide generation and trapping has been evaluated via methylidene transfer to a range of aldehydes to form epoxides.
引用
收藏
页码:8287 / 8290
页数:4
相关论文
共 17 条
  • [1] Aggarwal V.K., 1999, Comprehensive Asymmetric Catalysis II, P679
  • [2] Developments of asymmetric synthesis mediated by chiral sulfur reagents
    Blot, V
    Brière, JF
    Davoust, M
    Minière, S
    Reboul, V
    Metzner, P
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) : 1171 - 1182
  • [3] DECARBOXYLATION OF THETIN SALTS
    BURNESS, DM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (06) : 849 - 852
  • [4] Radical substituent effects of α-sulfonium groups
    Cheng, JP
    Liu, B
    Zhang, XM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7574 - 7575
  • [5] Instant methylide modification of the Corey-Chaykovsky epoxide synthesis
    Ciaccio, JA
    Drahus, AL
    Meis, RM
    Tingle, CT
    Smrtka, M
    Geneste, R
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (12) : 2135 - 2143
  • [6] COREY EJ, 1967, TETRAHEDRON LETT, P2325
  • [7] Stereoselective synthesis of three-membered ring compounds via ylide routes
    Dai, LX
    Hou, XL
    Zhou, YG
    [J]. PURE AND APPLIED CHEMISTRY, 1999, 71 (03) : 369 - 376
  • [8] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [9] Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes
    Forbes, DC
    Standen, MC
    Lewis, DL
    [J]. ORGANIC LETTERS, 2003, 5 (13) : 2283 - 2286
  • [10] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT)
    GOLOLOBOV, YG
    NESMEYANOV, AN
    LYSENKO, VP
    BOLDESKUL, IE
    [J]. TETRAHEDRON, 1987, 43 (12) : 2609 - 2651