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
  • [11] A novel synthesis of 5-aryl-3-phenylpyrazole from 2-aryl-3-benzoyl-1,1-cyclopropanedicarbonitrile and hydrazine
    Ren, ZJ
    Cao, WG
    Chen, J
    Wang, Y
    Ding, WY
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (02) : 495 - 497
  • [12] One-pot method for stereoselective cyclopropanation of electron-deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine
    Ren, ZJ
    Cao, WG
    Ding, WY
    Wang, Y
    [J]. SYNTHESIS-STUTTGART, 2005, (16): : 2718 - 2722
  • [13] Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in the presence of KF•2H2O
    Ren, ZJ
    Cao, WG
    Ding, WY
    Wang, Y
    Wang, LL
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (20) : 3785 - 3792
  • [14] Stereoselective synthesis of cis-1-carbomethoxy-2-aryl-3,3-dicyanocyclopropanes
    Ren, ZJ
    Ding, WY
    Cao, WG
    Wang, SH
    Huang, ZJ
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (20) : 3143 - 3148
  • [15] Ruano JLG, 2002, TETRAHEDRON-ASYMMETR, V13, P1993
  • [16] Ruano JLG, 2000, TETRAHEDRON-ASYMMETR, V11, P4737
  • [17] Tsuji T., 1987, CHEM CYCLOPROPYL GRO