Highly enantioselective rhodium-catalyzed conjugate addition of arylboronic acids to enones at room temperature

被引：27
|
作者：
Martina, SLX [1 ]
Minnaard, AJ [1 ]
Hessen, B [1 ]
Feringa, BL [1 ]
机构：
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 42期
关键词：
asymmetric 1,4-addition; arylboronic acid; rhodium-catalysis; phosphoramidite;
D O I：
10.1016/j.tetlet.2005.08.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rhodium-phosphoramidite-catalyzed asymmetric conjugate addition of arylboronic acids to enones proceeds at room temperature using [Rh(OH)(cod)](2) or [RhCl(cod)](2)/KOH as stable and readily available catalyst precursors. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码：7159 / 7163
页数：5
相关论文
共 50 条
  • [41] Rhodium-catalyzed conjugate addition-enantioselective protonation:: The synthesis of α,α'-dibenzyl esters
    Frost, Christopher G.
    Penrose, Stephen D.
    Lambshead, Kim
    Raithby, Paul R.
    Warren, John E.
    GleaveO, Robert
    [J]. ORGANIC LETTERS, 2007, 9 (11) : 2119 - 2122
  • [42] 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
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) : 9158 - 9164
  • [43] Rhodium-Catalyzed Enantioselective 1,6-Addition of Arylboronic Acids to Enynamides: Asymmetric Synthesis of Axially Chiral Allenylsilanes
    Nishimura, Takahiro
    Makino, Hiroki
    Nagaosa, Makoto
    Hayashi, Tamio
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12865 - 12867
  • [44] Bipyridyl-based diphosphine as an efficient ligand in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to α,β-unsaturated ketones
    Shi, Q
    Xu, LJ
    Li, XS
    Jia, X
    Wang, RH
    Au-Yeung, TTL
    Chan, ASC
    Hayashi, T
    Cao, R
    Hong, MC
    [J]. TETRAHEDRON LETTERS, 2003, 44 (34) : 6505 - 6508
  • [45] Rhodium-catalyzed enantioselective conjugate silyl transfer: 1,4-addition of silyl boronic esters to cyclic enones and lactones
    Walter, Christian
    Auer, Gertrud
    Oestreich, Martin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (34) : 5675 - 5677
  • [46] Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Phthaliminoacrylate Esters toward the Synthesis of β-Amino Acids
    Nishimura, Takahiro
    Wang, Jun
    Nagaosa, Makoto
    Okamoto, Kazuhiro
    Shintani, Ryo
    Kwong, Fuk-yee
    Yu, Wing-yiu
    Chan, Albert S. C.
    Hayashi, Tamio
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 464 - +
  • [47] Chiral tetrafluorobenzobarrelenes as highly efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids
    Nishimura, Takahiro
    Nagaosa, Makoto
    Hayashi, Tamio
    [J]. CHEMISTRY LETTERS, 2008, 37 (08) : 860 - 861
  • [48] Development of a palladium-catalyzed enantioselective conjugate addition of arylboronic acids to cyclic conjugate acceptors
    Holder, Jeffrey C.
    Kikushima, Kotaro
    Marziale, Alexander N.
    Gatti, Michele
    Stoltz, Brian M.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [49] Rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids
    Nishimura, T
    Hirabayashi, S
    Yasuhara, Y
    Hayashi, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2556 - 2557
  • [50] Rhodium-catalyzed addition of arylboronic acids to alkynyl aza-heteroaromatic compounds in water
    Lautens, M
    Yoshida, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03): : 762 - 769
12345