Enantioselective Diels-Alder reactions catalyzed by chiral magnesium Lewis acids prepared from hydroxysulfoxides

被引：37
|
作者：
Ordonez, M [1 ]
GuerrerodelaRosa, V [1 ]
Labastida, V [1 ]
Llera, JM [1 ]
机构：
[1] UNIV SEVILLA,FAC FARM,DEPT QUIM ORGAN & FARMACEUT,E-41071 SEVILLE,SPAIN
来源：
TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 09期
关键词：
D O I：
10.1016/0957-4166(96)00344-8
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Enantioselective Diels-Alder reactions were conducted successfully using chiral magnesium complexes prepared from magnesium iodide and chiral hydroxysulfoxides derived from (R)- and (S)-methyl 1-naphthyl sulfoxide. Convenient methods for the preparation of these chiral sulfoxides have also been developed. Hydroxysulfoxide 6 (and its enantiomer 10) showed the highest enantioselectivity. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：2675 / 2686
页数：12
相关论文
共 50 条
  • [21] α′-hydroxy enones as achiral templates for Lewis acid-catalyzed enantioselective Diels-Alder reactions
    Palomo, C
    Oiarbide, M
    García, JM
    González, A
    Arceo, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) : 13942 - 13943
  • [22] A three-center orbital interaction in the Diels-Alder reactions catalyzed by Lewis acids
    Yamabe, S
    Minato, T
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06): : 1830 - 1841
  • [23] Enantioselective Diels-Alder reactions catalyzed by samarium iodo binaphthoxides
    Giuseppone, N
    Santos, I
    Collin, J
    TETRAHEDRON LETTERS, 2000, 41 (05) : 639 - 642
  • [24] Enantioselective Diels-Alder reactions between cyclopentadiene and alpha,beta-acetylenic aldehydes catalyzed by a chiral super Lewis acid
    Corey, EJ
    Lee, TW
    TETRAHEDRON LETTERS, 1997, 38 (33) : 5755 - 5758
  • [25] ASYMMETRIC DIELS-ALDER REACTION OF CYCLOPENTADIENE AND METHYL ACRYLATE CATALYZED BY CHIRAL LEWIS-ACIDS
    KETTER, A
    GLAHSL, G
    HERRMANN, R
    JOURNAL OF CHEMICAL RESEARCH-S, 1990, (09): : 278 - 279
  • [26] Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels-Alder Reactions
    Varlet, Thomas
    Gelis, Coralie
    Retailleau, Pascal
    Bernadat, Guillaume
    Neuville, Luc
    Masson, Geraldine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (22) : 8491 - 8496
  • [27] Highly enantioselective azadiene Diels-Alder reactions catalyzed by chiral N-heterocyclic carbenes
    He, Ming
    Struble, Justin R.
    Bode, Jeffrey W.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) : 8418 - 8420
  • [28] Diels-Alder and dehydration reactions of furan derivatives with ethylene catalyzed by liquid Bronsted acids and Lewis acids
    Song, Song
    Wu, Guangjun
    Dai, Weili
    Guan, Naijia
    Li, Landong
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 420 : 134 - 141
  • [29] Enantioselective Diels-Alder reactions: NMR spectroscopy of a chiral titanium Lewis acid under high pressure
    Tietze, LF
    Ott, C
    Frey, U
    LIEBIGS ANNALEN, 1996, (01): : 63 - 67
  • [30] SILICA AND ALUMINA MODIFIED BY LEWIS-ACIDS AS CATALYSTS IN DIELS-ALDER REACTIONS OF CHIRAL ACRYLATES
    CATIVIELA, C
    FIGUERAS, F
    GARCIA, JI
    MAYORAL, JA
    PIRES, E
    ROYO, AJ
    TETRAHEDRON-ASYMMETRY, 1993, 4 (04) : 621 - 624
12345