Novel stereoselective syntheses of highly functionalized benzannulated pyrrolizidines and indolizidines by samarium diiodide induced cyclizations of indole derivatives

被引:67
作者
Gross, S [1 ]
Reissig, HU [1 ]
机构
[1] Free Univ Berlin, Inst Chem Organ Chem, D-14195 Berlin, Germany
关键词
D O I
10.1021/ol0355581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Suitably substituted heteroaromatic compounds such as indole and pyrrole derivatives are excellent acceptor units for intramolecular couplings of samarium ketyls. They furnish highly functionalized indole derivatives with very good diastereoselectivities additionally. Intermediate samarium enolates can be trapped by electrophiles, allowing efficient tandem reactions.
引用
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页码:4305 / 4307
页数:3
相关论文
共 33 条
  • [1] Banik BK, 2002, EUR J ORG CHEM, V2002, P2431
  • [2] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
    BECKWITH, ALJ
    [J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
  • [3] Berndt M, 2001, SYNLETT, P1290
  • [4] Berndt M., 2003, THESIS FREIE U BERLI
  • [5] Bonjoch J., 1996, ALKALOIDS, V48, P75
  • [6] Chadwick D. J., 1984, COMPREHENSIVE HETERO, V4, P155
  • [7] Dinesh CU, 1999, ANGEW CHEM INT EDIT, V38, P789, DOI 10.1002/(SICI)1521-3773(19990315)38:6<789::AID-ANIE789>3.0.CO
  • [8] 2-W
  • [9] DINESH CU, 1999, ANGEW CHEM, V111, P874
  • [10] DOPP H, 1994, HOUBENWEYL B, V6, P546