A cationic rhodium-chiral diene complex as a high-performance catalyst for the intramolecular asymmetric [4+2] cycloaddition of alkyne-1,3-dienes

被引：68
|
作者：
Shintani, Ryo [1 ]
Sannohe, Yuta [1 ]
Tsuji, Takaoki [1 ]
Hayashi, Tamio [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 38期
关键词：
asymmetric catalysis; cycloaddition; diene ligands; enantioselectivity; rhodium;
D O I：
10.1002/anie.200702586
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Two rings in one step: A rhodium-diene catalyst is more active than its rhodium-bisphosphine counterpart for the intramolecular [4+2] cycloaddition of alkyne-tethered 1,3-dienes (see scheme). A related complex with a C2-symmetric chiral diene ligand catalyzes an enantioselective asymmetric variant of this process. The intermolecular cycloaddition of 1,3-dienes and alkynes is also highly efficient. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7277 / 7280
页数：4
相关论文
共 16 条
  • [1] Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4+2] cycloaddition
    Aikawa, Kohsuke
    Akutagawa, Susumu
    Mikami, Koichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12648 - 12649
  • [2] Rhodium-catalyzed highly diastereoselective intramolecular [4+2] cycloaddition of 1,3-disubstituted allene-1,3-dienes
    Han, Yulin
    Ma, Shengming
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (18): : 2680 - 2684
  • [3] Rhodium-Catalyzed Dynamic Kinetic [4+2] Cycloaddition of Allene-1,3-Dienes
    Han, Yulin
    Qin, Anni
    Zhang, Qian
    Zhang, Xue
    Qian, Hui
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (47)
  • [4] ASYMMETRIC INDUCTION IN [4+2] CYCLOADDITIONS OF CHIRAL ENAMINES TO 2-PHENYLSULFONYL 1,3-DIENES
    BACKVALL, JE
    LOFSTROM, C
    MAFFEI, M
    LANGER, V
    TETRAHEDRON LETTERS, 1992, 33 (17) : 2417 - 2418
  • [5] Enantioselective [4+2] cycloaddition of buta-1,3-dienes to alkyl glyoxylates catalyzed by the chiral (salen)chromium(III) complex
    Kwiatkowski, P
    Asztemborska, M
    Caille, JC
    Jurczak, J
    ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (04) : 506 - 509
  • [6] One Stone for Three Birds-Rhodium-Catalyzed Highly Diastereoselective Intramolecular [4+2] Cycloaddition of Optically Active Allene-1,3-dienes
    Han, Yulin
    Qin, Anni
    Ma, Shengming
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (05) : 486 - 496
  • [7] Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4 + 2] cycloaddition
    Aikawa, Kohsuke
    Akutagawa, Susumu
    Mikami, Koichi
    Journal of the American Chemical Society, 2006, 128 (39): : 12648 - 12649
  • [8] Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne
    Huang, Suyu
    Li, Xiaoxun
    Lin, Claire L.
    Guzei, Ilia A.
    Tang, Weiping
    CHEMICAL COMMUNICATIONS, 2012, 48 (16) : 2204 - 2206
  • [9] The high-pressure [4+2] cycloaddition of activated 1,3-dienes to nonactivated heterodienophiles derived from glycolaldehyde
    Malinowska, M
    Salanski, P
    Caille, JC
    Jurczak, J
    SYNTHESIS-STUTTGART, 2002, (18): : 2707 - 2710
  • [10] 1ST [4+2] CYCLOADDITION REACTION BETWEEN VINYL FISCHER TYPE CARBENE COMPLEXES AND CHIRAL 2-AMINO-1,3-DIENES
    BARLUENGA, J
    AZNAR, F
    MARTIN, A
    BARLUENGA, S
    GARCIAGRANDA, S
    PANEQUEOUEVEDO, AA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) : 843 - 844
12