Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH••••O hydrogen bonding

被引：34
|
作者：
Paddon-Row, Michael N. [1 ]
Kwan, Laurence C. H. [2 ]
Willis, Anthony C. [2 ]
Sherburn, Michael S. [2 ]
机构：
[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia
[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 37期
关键词：
asymmetric catalysis; density functional calculations; Lewis acids; Lewis bases; transition states;
D O I：
10.1002/anie.200802002
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7013 / 7017
页数：5
相关论文
共 50 条
  • [41] Enantioselective Diels-Alder reactions of 3-(acyloxy)acrylates
    Sibi, MP
    Matsunaga, H
    TETRAHEDRON LETTERS, 2004, 45 (30) : 5925 - 5929
  • [42] Enantioselective Diels-Alder reactions catalyzed by chiral magnesium Lewis acids prepared from hydroxysulfoxides
    Ordonez, M
    GuerrerodelaRosa, V
    Labastida, V
    Llera, JM
    TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2675 - 2686
  • [43] Enantioselective Diels-Alder reactions of 3-(acyloxy)acrylates
    Matsunaga, H
    Sibi, MP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U361 - U361
  • [44] N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions
    Corminboeuf, O
    Renaud, P
    ORGANIC LETTERS, 2002, 4 (10) : 1735 - 1738
  • [45] Enantioselective Diels-Alder Reactions of Enals and Alkylidene Diketones Catalyzed by N-Heterocyclic Carbenes
    Fang, Xinqiang
    Chen, Xingkuan
    Chi, Yonggui Robin
    ORGANIC LETTERS, 2011, 13 (17) : 4708 - 4711
  • [46] ENFORCED HYDROPHOBIC INTERACTIONS AND HYDROGEN-BONDING IN THE ACCELERATION OF DIELS-ALDER REACTIONS IN WATER
    BLOKZIJL, W
    ENGBERTS, JBFN
    STRUCTURE AND REACTIVITY IN AQUEOUS SOLUTION: CHARACTERIZATION OF CHEMICAL AND BIOLOGICAL SYSTEMS, 1994, 568 : 303 - 317
  • [47] Catalytic enantioselective aza Diels-Alder reactions of imino dienophiles
    Yao, SL
    Johannsen, M
    Hazell, RG
    Jorgensen, KA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (22) : 3121 - 3124
  • [48] On the importance of hydrogen bonding in the promotion of Diels-Alder reactions of unactivated aldehydes: a computational study
    Chemouri, Hafida
    Mekelleche, Sidi Mohamed
    MOLECULAR PHYSICS, 2014, 112 (5-6) : 601 - 608
  • [49] Hydrogen bonding catalysis operates by charge stabilization in highly polar diels-alder reactions
    Gordillo, Ruth
    Dudding, Travis
    Anderson, Christopher D.
    Houk, K. N.
    ORGANIC LETTERS, 2007, 9 (03) : 501 - 503
  • [50] Hydrophobic and hydrogen-bonding effects on the rate of Diels-Alder reactions in aqueous solution
    Furlani, TR
    Gao, JL
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16): : 5492 - 5497
12345