Diastereoselective synthesis of highly substituted tetrahydropyran-4-ones

被引:41
作者
Clarke, PA [1 ]
Martin, WHC [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1021/ol027081j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Aldol reactions of beta-ketoesters with aldehydes followed by a tandem Knoevenagel condensation, with a further equivalent of aldehyde, and intramolecular Michael addition produces single diastereomers of highly substituted tetrahydropyran-4-ones.
引用
收藏
页码:4527 / 4529
页数:3
相关论文
共 21 条
  • [1] ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
  • [2] STEREOCHEMISTRY AND STRUCTURE IN TETRAHYDRO-1-THIO-4-PYRONE AND TETRAHYDRO-4-PYRONE SERIES
    BAXTER, CAR
    WHITING, DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09): : 1174 - &
  • [3] Boger D. L., 1987, HETERO DIELS ALDER M
  • [4] Stereocontrolled synthesis of trisubstituted tetrahydropyrans
    Cloninger, MJ
    Overman, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) : 1092 - 1093
  • [5] COMUBERT R, 1934, B CHIM SOC FR, P90
  • [6] Oxonia-cope rearrangement and side-chain exchange in the prins cyclization
    Crosby, SR
    Harding, JR
    King, CD
    Parker, GD
    Willis, CL
    [J]. ORGANIC LETTERS, 2002, 4 (04) : 577 - 580
  • [7] Dossetter AG, 1999, ANGEW CHEM INT EDIT, V38, P2398, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2398::AID-ANIE2398>3.0.CO
  • [8] 2-E
  • [9] Hanessian S., 1983, TOTAL SYNTHESIS NATU
  • [10] ALDOL TYPE CONDENSATIONS OF BETA-KETO ESTER DIANIONS
    HUCKIN, SN
    WEILER, L
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (11): : 2157 - 2164