Planar chiral imidazolium salts in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes

被引:110
|
作者
Focken, T [1 ]
Rudolph, J [1 ]
Bolm, C [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
来源
SYNTHESIS-STUTTGART | 2005年 / 03期
关键词
2.2]paracyclophane; N-heterocyclic carbene; imidazolium salt; asymmetric catalysis; boronic acid; diarylmethanol;
D O I
10.1055/s-2005-861800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Planar chiral imidazolium salts 8 and 13 were used as precursors for N-heterocyclic carbene ligands, which were applied in rhodium-catalyzed additions of arylboronic acids to aromatic aldehydes. With pseudo-ortho-disubstituted [2.2]paracyclophane (S,R-p)-8b bearing a phosphinoyl substituent at the paracyclophane backbone, 38% ee has been achieved in this rather unexplored reaction.
引用
收藏
页码:429 / 436
页数:8
相关论文
共 50 条
  • [1] Planar chiral imidazolium salts based on [2.2]paracyclophane in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes
    Ma, Qingshuang
    Ma, Yudao
    Liu, Xiao
    Duan, Wenzeng
    Qu, Bo
    Song, Chun
    TETRAHEDRON-ASYMMETRY, 2010, 21 (03) : 292 - 298
  • [2] ORGN 435-Novel planar chiral imidazolium salts in the asymmetric rhodium-catalyzed addition of arylboronic acids to aldehydes
    Ma, Qingshuang
    Ma, Yudao
    Duan, Wenzeng
    Xia, Houqi
    Song, Chun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [3] Novel hexadentate imidazolium salts in the rhodium-catalyzed addition of arylboronic acids to aldehydes
    Chen, JH
    Zhang, XQ
    Feng, Q
    Luo, MM
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (03) : 470 - 474
  • [4] Rhodium-catalyzed diastereoselective 1,2-addition of arylboronic acids to chiral trifluoroethyl imine
    Truong, Vouy Linh
    Pfeiffer, Jennifer Y.
    TETRAHEDRON LETTERS, 2009, 50 (14) : 1633 - 1635
  • [5] Chiral Sulfinamide-Olefin Ligands: Switchable Selectivity in Rhodium-Catalyzed Asymmetric 1,2-Addition of Arylboronic Acids to Aliphatic -Ketoesters
    Zhu, Ting-Shun
    Xu, Ming-Hua
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (03) : 321 - 328
  • [6] ORGN 401-Application of rhodium chiral dicyclophane imidazolium carbene catalyst in 1,2-addition of arylboronic acids to aldehydes
    Ma, Yudao, Sr.
    Chai, Qiang
    Zhou, Tong
    Sun, Zhijun
    Huang, Minghu
    Liu, Xueying
    Duan, Wenzeng
    Song, Chun
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [7] Complete Stereoretention in the Rhodium-Catalyzed 1,2-Addition of Chiral Secondary and Tertiary Alkyl Potassium Trifluoroborate Salts to Aldehydes
    Ros, Abel
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (34) : 6289 - 6292
  • [8] Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Indolylnitroalkenes
    Xing, Junwei
    Chen, Guihua
    Cao, Peng
    Liao, Jian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (06) : 1230 - 1236
  • [9] Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters
    Wang, Hui
    Zhu, Ting-Shun
    Xu, Ming-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) : 9158 - 9164
  • [10] Enantioselective rhodium-catalyzed addition of arylboronic acids to aldehydes using chiral spiro monophosphite ligands
    Duan, HF
    Xie, JH
    Shi, WJ
    Zhang, Q
    Zhou, QL
    ORGANIC LETTERS, 2006, 8 (07) : 1479 - 1481