A catalytic carbon-phosphorus ylide reaction: Phosphane-catalyzed annulation of allylic compounds with electron-deficient alkenes

被引：223
作者：
Du, YH [1 ]
Lu, XY [1 ]
Zhang, CM [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 09期
关键词：
D O I：
10.1002/anie.200390266
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Readily available starting materials and high selectivity: These are two appealing features of the phosphane-catalyzed carbon-phosphorus ylide reaction described. Bromide, acetate, of tert-butyl carbonate derivatives of adducts formed by the Morita-Baylis-Hillman reaction react with PPh3 to form an allylic ylide. Phosphane-catalyzed annulation of the ylides with electron-deficient alkenes results in the facile construction of cyclopentenes [Eq. (1)]. X = Br, OAc, OBoc; E = CO2Et.
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页码：1035 / +
页数：4
相关论文
共 41 条
  • [1] Aggarwal V. K., 2001, ANGEW CHEM, V113, P1482
  • [2] Aggarwal VK, 1998, SYNLETT, P329
  • [3] Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO
  • [4] 2-W
  • [5] Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
  • [6] 2-E
  • [7] NEW SYNTHESIS OF CYCLOHEXADIENE DERIVATIVES
    BOHLMANN, F
    ZDERO, C
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (12): : 3779 - 3787
  • [8] SYNTHETIC STUDIES ON DAMASCENONES
    BUCHI, G
    WUEST, H
    [J]. HELVETICA CHIMICA ACTA, 1971, 54 (07) : 1767 - &
  • [9] DAUBEN WG, 1973, TETRAHEDRON LETT, P4425
  • [10] DAUBEN WG, 1973, TETRAHEDRON LETT, P3711
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