Stereoselective synthesis of highly substituted trans-2,3-dihydrofuran and trans-1,2-cyclopropane derivatives containing sulfonyl groups

被引:38
作者
Cao, Weiguo [1 ,2 ]
Zhang, Hui [1 ]
Chen, Jie [1 ]
Zhou, Xiaohong [1 ]
Shao, Min [3 ]
McMills, Mark C. [4 ]
机构
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[3] Shanghai Univ, Inst Anal & Res Ctr, Shanghai 200444, Peoples R China
[4] Ohio Univ, Dept Chem & Biochem, Athens, OH 45701 USA
基金
中国国家自然科学基金; 上海市自然科学基金;
关键词
D O I
10.1016/j.tet.2007.10.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
trans-2,3-Dihydrofuran derivatives 3 and trans-1,2-cyclopropane derivatives 4 were prepared with high chemoselectivity and moderate overall chemical yield by the reaction of alpha,beta-unsaturated sulfones 1 with arsonium bromides 2 in the presence of potassium carbonate. The structures of products obtained were identified by IR, MS, (1)H NMR, elemental analysis, and X-ray diffraction analysis. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:163 / 167
页数:5
相关论文
共 17 条
  • [1] Simple approach to the high stereoselective synthesis of trans-2,3-dihydrofuran derivatives
    Cao, WG
    Chen, GD
    Chen, J
    Chen, RQ
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (04) : 527 - 533
  • [2] A highly stereoselective synthesis of 2,3,4,5-tetrasubstituted-trans-2,3-dihydrofurans
    Cao, WG
    Ding, WY
    Chen, J
    Chen, YL
    Zang, Q
    Chen, GD
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (09) : 1599 - 1608
  • [3] A facile synthesis of dimethyl 4-(alpha-furyl)- and 4-(alpha-thienyl)-6-perfluoroalkylisophthalates via acyclic precursors
    Cao, WG
    Ding, WY
    Ding, WL
    Huang, H
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1997, 83 (01) : 21 - 26
  • [4] High stereoselective synthesis of trans-2,3-dihydrofuran derivatives
    Chen, GD
    Cao, WG
    Chen, J
    Chen, RQ
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (20) : 3793 - 3799
  • [5] DEMEIJERE A, 2000, SMALL RING COMPOUN 6, V27
  • [6] DING W, 2000, Z CHEM J CHIN U, V21, P64
  • [7] Alkynyliodonium salts in organic synthesis. Dihydrofuran formation via a formal stevens shift of a carbon substituent within a disubstituted-carbon oxonium ylide
    Feldman, KS
    Wrobleski, ML
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8659 - 8668
  • [8] The first asymmetric cyclopropanation reactions involving a stable carbene
    Krysiak, J
    Kato, T
    Gornitzka, H
    Baceiredo, A
    Mikolajczyk, M
    Bertrand, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) : 8240 - 8242
  • [9] Stereoselective cyclopropanation reactions
    Lebel, H
    Marcoux, JF
    Molinaro, C
    Charette, AB
    [J]. CHEMICAL REVIEWS, 2003, 103 (04) : 977 - 1050
  • [10] LEE JW, 1990, HETEROCYCLES, V31, P1417