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
  • [1] Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions
    Lehmler, H.-J.
    Nieger, M.
    Breitmaier, E.
    Synthesis, (01):
  • [2] Tricarbonyls: Reactive model dienophiles for asymmetric Diels-Alder reactions
    Lehmler, HJ
    Nieger, M
    Breitmaier, E
    SYNTHESIS-STUTTGART, 1996, (01): : 105 - +
  • [3] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL ISOPRENYL ETHERS WITH REACTIVE DIENOPHILES
    THIEM, R
    ROTSCHEIDT, K
    BREITMAIER, E
    SYNTHESIS-STUTTGART, 1989, (11): : 836 - 843
  • [4] 2-Nitrofurans as dienophiles in Diels-Alder reactions
    Della Rosa, C
    Kneeteman, MN
    Mancini, PME
    TETRAHEDRON LETTERS, 2005, 46 (50) : 8711 - 8714
  • [5] Asymmetric Diels-Alder reactions with chiral acetylenic carbene complexes as dienophiles
    Rahm, A
    Rheingold, AL
    Wulff, WD
    TETRAHEDRON, 2000, 56 (28) : 4951 - 4965
  • [6] PROPARGYL CATIONS - POWERFUL AMBIENT-TEMPERATURE DIENOPHILES IN THE DIELS-ALDER REACTION
    GASSMAN, PG
    SINGLETON, DA
    TETRAHEDRON LETTERS, 1987, 28 (48) : 5969 - 5972
  • [7] DIELS-ALDER REACTIONS WITH 2-CARBON SULFUR DIENOPHILES
    WENKERT, E
    BROKA, CA
    FINNISH CHEMICAL LETTERS, 1984, (4-5): : 126 - 129
  • [8] ASYMMETRIC DIELS-ALDER REACTIONS OF SOME CHIRAL DIENOPHILES DERIVED FROM CINCHONA ALKALOIDS
    SUZUKI, H
    MOCHIZUKI, K
    HATTORI, T
    TAKAHASHI, N
    TAJIMA, O
    TAKIGUCHI, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (06) : 1999 - 2005
  • [9] N-ACRYLOYL-L-PHENYLALANINE DERIVATIVES AS DIENOPHILES IN ASYMMETRIC DIELS-ALDER REACTIONS
    AVENOZA, A
    BUENO, MP
    CATIVIELA, C
    MAYORAL, JA
    ANALES DE QUIMICA-INTERNATIONAL EDITION, 1992, 88 (02): : 249 - 252
  • [10] CHIRAL 2-VINYL-1,3,2-OXAZAPHOSPHOLIDIN-2-ONES - NEW DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS
    KATAGIRI, N
    YAMAMOTO, M
    IWAOKA, T
    KANEKO, C
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (20) : 1429 - 1430
12345