Tandem retro-aldol/Wittig/Michael and related cascade processes

被引:10
作者
Beltran-Rodil, Sandra [1 ]
Donald, James R. [1 ]
Edwards, Michael G. [1 ]
Raw, Steven A. [2 ]
Taylor, Richard J. K. [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] AstraZeneca, Proc Res & Dev, Macclesfield SK10 2NA, Cheshire, England
关键词
OXIDATION PROCESSES; SEQUENCES;
D O I
10.1016/j.tetlet.2009.02.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of novel tandem sequences initiated by a retro-aldol process are described along with preliminary scope and limitation studies. These include (i) retro-aldol/Wittig trapping/intramolecular Michael addition, (ii) retro-aldol/aza-Wittig/intramolecular imine addition, (iii) retro-aldol/Henry/intramolecular Michael addition and (iv) retro-aldol/Knoevenagel/intramolecular Michael addition sequences. A range of novel functionalised cyclopentanes, and related systems, are described which should prove to be useful synthetic building blocks. (C) 2009 Elsevier Ltd. All Fights reserved.
引用
收藏
页码:3378 / 3380
页数:3
相关论文
共 21 条
  • [1] Tandem inverse electron demand Diels-Alder, retro-Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles
    Bromley, William J.
    Gibson, Mairi
    Lang, Stuart
    Raw, Steven A.
    Whitwood, Adrian C.
    Taylor, Richard J. K.
    [J]. TETRAHEDRON, 2007, 63 (26) : 6004 - 6014
  • [2] Deacetalisation-bicyclisation routes to novel polycyclic heterocycles using stannous chloride dihydrate
    Cayley, Alex N.
    Cox, Rhona J.
    Menard-Moyon, Cecilia
    Schmidt, Jan Peter
    Taylor, Richard J. K.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (37) : 6556 - 6560
  • [3] Conti Paola, 2003, Farmaco (Lausanne), V58, P683, DOI 10.1016/S0014-827X(03)00107-1
  • [4] Craig D, 1997, SYNLETT, P1001
  • [5] Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides
    Donald, James R.
    Edwards, Michael G.
    Taylor, Richard J. K.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (30) : 5201 - 5204
  • [6] Tandem Meinwald Rearrangement-Fischer Indolisation: A One-Pot Conversion of Epoxides into Indoles
    Donald, James R.
    Taylor, Richard J. K.
    [J]. SYNLETT, 2009, (01) : 59 - 62
  • [7] DZHAFAROV MK, 1992, RUSS CHEM REV, V61, P363
  • [8] Synthesis of functionalized pyrrolidin-2-ones and (S)-Vigabatrin from pyrrole
    Gheorghe, A
    Schulte, M
    Reiser, O
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) : 2173 - 2176
  • [9] HYDROFORMYLATION OF 1,6-DIENES WITH CARBONYLHYDRIDOTRIS(TRIPHENYLPHOSPHINE)RHODIUM
    GRIGG, R
    REIMER, GJ
    WADE, AR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08): : 1929 - 1935
  • [10] VILSMEIER-HAACK REACTION WITH SUCCINAMIDALS - A CONVENIENT SYNTHESIS OF 5-CHLOROPYRROLE-2-CARBOXALDEHYDES AND 5-CHLOROPYRROLE-2,4-DICARBOXALDEHYDES
    GUZMAN, A
    ROMERO, M
    MUCHOWSKI, JM
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (05): : 791 - 794