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
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
  • [21] CATALYTIC ASYMMETRIC CARBONYL-ENE REACTIONS
    BERRISFORD, DJ
    BOLM, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16): : 1717 - 1719
  • [22] Indium(III) complex-catalyzed tandem carbonyl-ene reaction: An efficient construction of tetrahydropyran rings
    Loh, TP
    Feng, LC
    Yang, JY
    SYNTHESIS-STUTTGART, 2002, (07): : 937 - 940
  • [23] Indium(III) complex-catalyzed tandem carbonyl-ene reaction: An efficient construction of tetrahydropyran rings
    Loh, Teck-Peng
    Feng, Li-Chun
    Yang, Jian-Ying
    Synthesis, 2002, (07) : 937 - 940
  • [24] Highly enantioselective carbonyl-ene reaction catalyzed by chiral titanium complexes: Toward structural elucidation of catalytically active species
    Terada, Masahiro
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (08) : 748 - 760
  • [25] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE CATALYSIS OF THE CARBONYL-ENE REACTION WITH FLUORAL
    MIKAMI, K
    YAJIMA, T
    TERADA, M
    KATO, E
    MARUTA, M
    TETRAHEDRON-ASYMMETRY, 1994, 5 (06) : 1087 - 1090
  • [26] BiCl3-catalyzed Mukaiyama-aldol and carbonyl-ene reactions
    Peidro, L
    LeRoux, C
    Laporterie, A
    Dubac, J
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 521 (1-2) : 397 - 399
  • [27] Self-supported heterogeneous titanium catalysts for enantioselective carbonyl-ene and sulfoxidation reactions
    Wang, XS
    Wang, XW
    Guo, HC
    Wang, Z
    Ding, KL
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (14) : 4078 - 4088
  • [28] Asymmetric carbonyl-ene reaction of trifluoropyruvate catalyzed by Pd(II)-SunPhos complex
    Jiang, Lili
    Hu, Bei
    Xie, Xiaomin
    Zhang, Zhaoguo
    TETRAHEDRON, 2017, 73 (49) : 6901 - 6905
  • [29] Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction
    Luo, Weiwei
    Lin, Lili
    Zhang, Yu
    Liu, Xiaohua
    Feng, Xiaoming
    ORGANIC LETTERS, 2017, 19 (13) : 3374 - 3377
  • [30] Enantioselective Cationic Polyene Cyclization vs Enantioselective Intramolecular Carbonyl-Ene Reaction
    Zhao, Yu-Jun
    Li, Bin
    Tan, Li-Jun Serena
    Shen, Zhi-Liang
    Loh, Teck-Peng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) : 10242 - 10244