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
  • [31] Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts
    Peng, Zhili
    Narcis, Maurice J.
    Takenaka, Norito
    MOLECULES, 2013, 18 (08) : 9982 - 9998
  • [32] An Efficient Cyclic Di-AMP Based Artificial Metalloribozyme for Enantioselective Diels-Alder Reactions
    Qi, Qianqian
    Lv, Shuting
    Hao, Min
    Dong, Xingchen
    Gu, Youkun
    Wu, Peizhe
    Zhang, Wenyue
    Chen, Yashao
    Wang, Changhao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (28) : 4417 - 4424
  • [33] 31P NMR Spectroscopically Quantified Hydrogen-Bonding Strength of Thioureas and Their Catalytic Activity in Diels-Alder Reactions
    Noedling, Alexander R.
    Jakab, Gergely
    Schreiner, Peter R.
    Hilt, Gerhard
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6394 - 6398
  • [34] 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
  • [35] Isotope effects for Lewis acid catalyzed Diels-Alder reactions. The experimental transition state
    Singleton, DA
    Merrigan, SR
    Beno, BR
    Houk, KN
    TETRAHEDRON LETTERS, 1999, 40 (32) : 5817 - 5821
  • [36] Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions
    Futatsugi, K
    Yamamoto, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1484 - 1487
  • [37] Ethylene-bridged bissulfoximines in copper-catalyzed enantioselective hetero-Diels-Alder reactions
    Bolm, C
    Verrucci, M
    Simic, O
    Hackenberger, CPR
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1696 - 1700
  • [38] Enantioselective Diels-Alder reactions with left-handed G-quadruplex DNA-based catalysts
    Chen, Kun
    He, Zhiyong
    Xiong, Wei
    Wang, Chun-Jiang
    Zhou, Xiang
    CHINESE CHEMICAL LETTERS, 2021, 32 (05) : 1701 - 1704
  • [39] Enantioselective Diels-Alder Reactions with Anomalous endo/exo Selectivities Using Conformationally Flexible Chiral Supramolecular Catalysts
    Hatano, Manabu
    Mizuno, Tomokazu
    Izumiseki, Atsuto
    Usami, Ryota
    Asai, Takafumi
    Akakura, Matsujiro
    Ishihara, Kazuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) : 12189 - 12192
  • [40] Asymmetric Diels-Alder reactions of α′-benzenesulfonyl-α,β-unsaturated ketones with cyclopentadiene catalyzed by a chiral titanium reagent
    Pei, W
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1998, 19 (03): : 402 - 405
12345