2-Alkenyl dioxolanylium cations, new reactive dienophiles in low temperature asymmetric Diels-Alder reactions

被引：13
|
作者：
Haudrechy, A [1 ]
Picoul, W [1 ]
Langlois, Y [1 ]
机构：
[1] UNIV PARIS 11,ICMO,LAB SYNTH SUBST NAT,CNRS,F-91405 ORSAY,FRANCE
来源：
TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 01期
关键词：
D O I：
10.1016/S0957-4166(96)00470-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Chiral orthoesters 14-22 were prepared by an exchange reaction with orthoester 13. These compounds, after treatment with trimethylsilyltriflate or tin(IV) chloride, gave rise to vinyl dioxolanylium cations which proved to be very reactive dienophiles in various Diels-Alder reactions. (C) 1997, Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：139 / 148
页数：10
相关论文
共 50 条
  • [41] C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions
    Ma, Yuanhui
    Zhang, Yong Jian
    Jin, Shangbin
    Li, Qiqi
    Li, Chenguang
    Lee, Junseong
    Zhang, Wanbin
    TETRAHEDRON LETTERS, 2009, 50 (52) : 7388 - 7391
  • [42] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL (E)-2-CYANOCINNAMATES WITH CYCLOPENTADIENE
    CATIVIELA, C
    MAYORAL, JA
    AVENOZA, A
    PEREGRINA, JM
    LAHOZ, FJ
    GIMENO, S
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17): : 4664 - 4669
  • [43] Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst
    Wang, Yi
    Li, Hongming
    Wang, Yong-Qiang
    Liu, Yan
    Foxman, Bruce M.
    Deng, Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (20) : 6364 - +
  • [44] REACTIONS OF COORDINATED MOLECULES .42. DIELS-ALDER REACTIONS UTILIZING (FERRA-BETA-DIKETONATO)BF2 COMPLEXES CONTAINING ALKENYL SUBSTITUENTS AS ACTIVATED DIENOPHILES
    LENHERT, PG
    LUKEHART, CM
    SACKSTEDER, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) : 793 - 800
  • [45] Asymmetric Lewis acid mediated hetero Diels-Alder reactions with 2H-azirines as dienophiles -: An efficient route to substituted tetrahydropyridines.
    Somfai, P
    Timén, AS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U161 - U161
  • [46] Asymmetric Diels-Alder reactions of chiral cyclopropylidene imide dienophiles:: Preparation of gem-dimethyl- and spirocyclopropane norbornyl carboxylic acids
    Kuethe, JT
    Zhao, DL
    Humphrey, GR
    Journet, M
    McKeown, AE
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 2192 - 2195
  • [47] DIELS-ALDER REACTIONS .2. INDEPENDENCE OF REACTION TEMPERATURE AND MODE OF ADDITION IN ISOPRENE-METHYL ACRYLATE DIELS-ALDER REACTION
    HENNIS, HE
    JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10): : 2570 - &
  • [48] LOW COORDINATED PHOSPHORUS-COMPOUNDS .29. DIELS-ALDER REACTIONS OF 2,3-DIMETHYLBUTADIENE WITH STABLE PHOSPHAALKENES AS DIENOPHILES
    APPEL, R
    KNOCH, F
    ZIMMERMANN, R
    CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (02): : 814 - 824
  • [49] SYNTHESIS AND DIELS-ALDER REACTIONS OF 5-ALKENYL-(3H)-2-FURANONES
    ALEXANDRE, C
    BERTHO, C
    TABTI, B
    ROUESSAC, F
    TETRAHEDRON, 1991, 47 (29) : 5481 - 5490
  • [50] PREPARATION AND DIELS-ALDER REACTIONS OF 5-ALKENYL 2-(3H)-FURANONES
    ALEXANDRE, C
    ROUESSAC, F
    TABTI, B
    TETRAHEDRON LETTERS, 1985, 26 (44) : 5453 - 5456
12345