Highly Enantioselective Carbonyl-ene Reactions Catalyzed by In(III)-PyBox Complex

被引：60
|
作者：
Zhao, Jun-Feng [1 ]
Tsui, Hoi-Yan [1 ]
Wu, Pei-Jia [1 ]
Lu, Jun [1 ]
Loh, Teck-Peng [1 ]
机构：
[1] Nanyang Technol Univ, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 49期
关键词：
D O I：
10.1021/ja807501a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly enantioselective carbonyl-ene reaction catalyzed by In(III)-pybox is described. Both 1, 1-disubstituted alkenes and 1,1,2-trisubstituted alkenes proceeded smoothly to give the ene products in high yields up to 97% and with excellent diastereoselectivity and enantioselectivities up to > 99:1 and 99%, respectively.
引用
收藏
页码：16492 / +
页数：3
相关论文
共 50 条
  • [1] Highly enantioselective carbonyl-ene reactions catalyzed by In(III)-PyBox complex
    Zhao, Jun-Feng
    Tsui, Hoi-Yan
    Wu, Pei-Jia
    Lu, Jun
    Loh, Teck-Peng
    Journal of the American Chemical Society, 2008, 130 (49): : 16492 - 16493
  • [2] In(III)-PyBox complex catalyzed highly enantioselective carbonyl-ene reactions
    Zhao, Jun-Feng, Sr.
    Loh, Teck Peng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [3] Significant counterion effect of the In(III)-pybox complex in highly enantioselective carbonyl-ene reactions of ethyl glyoxylate
    Zhao, Jun-Feng
    Tjan, Teguh-Budiono W.
    Loh, Teck-Peng
    TETRAHEDRON LETTERS, 2010, 51 (43) : 5649 - 5652
  • [4] Enantioselective Carbonyl-Ene Reactions of Trifluoropyruvate in Ionic Liquid via a Recyclable Indium(III)-Pybox Complex
    Zhao, Jun Feng
    Tan, Boon Hong
    Zhu, Ming Kui
    Tjan, Teguh Budiono W.
    Loh, Teck Peng
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) : 2085 - 2088
  • [5] Highly enantioselective carbonyl-ene reactions catalyzed by a hindered silyl-salen-cobalt complex
    Hutson, Gerri E.
    Dave, Apurva H.
    Rawal, Viresh H.
    ORGANIC LETTERS, 2007, 9 (20) : 3869 - 3872
  • [6] Enantioselective Carbonyl-Ene Reactions Catalyzed by Chiral Cationic Dirhodium(II,III) Carboxamidates
    Xu, Xichen
    Wang, Xiaochen
    Liu, Yuxiao
    Doyle, Michael P.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24): : 12185 - 12190
  • [7] Enantioselective catalytic carbonyl-ene cyclization reactions
    Grachan, Melissa L.
    Tudge, Matthew T.
    Jacobsen, Eric. N.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) : 1469 - 1472
  • [8] Assembled enantioselective catalysts for carbonyl-ene reactions
    Guo, HC
    Wang, XW
    Ding, KL
    TETRAHEDRON LETTERS, 2004, 45 (09) : 2009 - 2012
  • [9] Intramolecular carbonyl-ene reactions catalyzed by a triflylphosphoramide
    Davis, Lindsey
    Santos, Maria
    Dahlmann, Heidi
    McKinney, Amanda
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [10] Highly Enantioselective Ketone-Ene Reactions of Trifluoropyruvate: Significant Counterion Effect of the In(III)-PyBox Complex
    Zhao, Jun-Feng
    Tjan, Teguh-Budiono W.
    Tan, Boon-Hong
    Loh, Teck-Peng
    ORGANIC LETTERS, 2009, 11 (24) : 5714 - 5716
12345