Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds

被引:148
|
作者
Shintani, R [1 ]
Ueyama, K [1 ]
Yamada, I [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
D O I
10.1021/ol048421z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.
引用
收藏
页码:3425 / 3427
页数:3
相关论文
共 50 条
  • [1] Chiral tetrafluorobenzobarrelenes as highly efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids
    Nishimura, Takahiro
    Nagaosa, Makoto
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2008, 37 (08) : 860 - 861
  • [2] Chiral Heterodisulfoxide Ligands in Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromenones
    Han, Fuzhong
    Chen, Guihua
    Zhang, Xiangyang
    Liao, Jian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) : 2928 - 2931
  • [3] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine
    Chen, G
    Tokunaga, N
    Hayashi, T
    ORGANIC LETTERS, 2005, 7 (11) : 2285 - 2288
  • [4] Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds:: Large accelerating effects of bases and ligands
    Itooka, R
    Iguchi, Y
    Miyaura, N
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15): : 6000 - 6004
  • [5] Effect of Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Sulfonyl Compounds
    Nishimura, Takahiro
    Takiguchi, Yuka
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9086 - 9089
  • [6] Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions
    Duan, Wei-Liang
    Iwamura, Hiroshi
    Shintani, Ryo
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 2130 - 2138
  • [7] Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates
    Soergel, Sebastian
    Tokunaga, Norihito
    Sasaki, Keigo
    Okamoto, Kazuhiro
    Hayashi, Tamio
    ORGANIC LETTERS, 2008, 10 (04) : 589 - 592
  • [8] Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated amides
    Sakuma, S
    Miyaura, N
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8944 - 8946
  • [9] Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes catalyzed by a chiral diene-rhodium complex
    Hayashi, T
    Tokunaga, N
    Okamoto, K
    Shintani, R
    CHEMISTRY LETTERS, 2005, 34 (11) : 1480 - 1481
  • [10] Rhodium catalyzed asymmetric 1,4-addition of arylboronic acids to β,γ-unsaturated α-keto ester using chiral tert-butanesulfinylphosphines ligands
    Wang, Juanjuan
    Wang, Bing
    Cao, Peng
    Liao, Jian
    TETRAHEDRON LETTERS, 2014, 55 (23) : 3450 - 3453