Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates

被引:45
作者
Brown, PM [1 ]
Käppel, N [1 ]
Murphy, PJ [1 ]
机构
[1] Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales
关键词
tandem reactions; Michael additions;
D O I
10.1016/S0040-4039(02)02142-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tri-n-Butyl phosphine was found to effect tandem Michael/Michael cyclisations leading to the formation of cyclopentenes and cyclohexenes in good yields, whilst p-TolSH in conjunction with a catalytic amount of p-TolSNa effected cyclisation to the corresponding cyclopentanes and cyclohexanes. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:8707 / 8710
页数:4
相关论文
共 25 条
  • [1] An intramolecular Baylis-Hillman reaction catalysed by secondary amines
    Black, GP
    Dinon, F
    Fratucello, S
    Murphy, PJ
    Nielsen, M
    Williams, HL
    [J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8561 - 8564
  • [2] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
    Black, GP
    Murphy, PJ
    Walshe, NDA
    [J]. TETRAHEDRON, 1998, 54 (32) : 9481 - 9488
  • [3] TANDEM FREE-RADICAL ALKENE ADDITION-REACTIONS OF ACYL RADICALS
    BOGER, DL
    MATHVINK, RJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4003 - 4008
  • [4] Asymmetric synthesis of β-amino acid scaffolds
    Bull, SD
    Davies, SG
    Smith, AD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (22): : 2931 - 2938
  • [5] Facile synthesis of a key intermediate for the synthesis of prostanes and isoprostanes
    Chavan, SP
    Subbarao, YT
    Chittiboyina, AG
    Sivappa, R
    Suresh, CG
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (08) : 1101 - 1103
  • [6] STEREOSELECTIVE CONSTRUCTION OF FUNCTIONALIZED BICYCLIC CARBOCYCLES THROUGH METAL-HALOGEN EXCHANGE-INITIATED SEQUENTIAL CONJUGATE ADDITION-REACTIONS
    COOKE, MP
    GOPAL, D
    [J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2837 - 2840
  • [7] Tandem Michael/intramolecular aldol reactions mediated by secondary amines, thiols and phosphines
    Dinon, F
    Richards, E
    Murphy, PJ
    Hibbs, DE
    Hursthouse, MB
    Abdul Malik, KM
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3279 - 3282
  • [8] A new tandem route to angular tetraquinanes. Synthesis of the waihoensene ring system
    ErgUden, JK
    Moore, HW
    [J]. ORGANIC LETTERS, 1999, 1 (03) : 375 - 377
  • [9] The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts
    Frank, SA
    Mergott, DJ
    Roush, WR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2404 - 2405
  • [10] KLIMKO PG, 1994, SYNTHESIS-STUTTGART, P979