Platinum-Catalyzed Asymmetric Ring-opening Reaction of Oxabenzonorbornadiene with Terminal Alkynes

被引：9
作者：
Long, Yuhua [1 ]
Jiang, Han [1 ]
Zou, Zhifu [1 ]
Chen, Kaixuan [1 ]
Fang, Yali [1 ]
机构：
[1] S China Normal Univ, Sch Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2014年 / 32卷 / 07期
基金：
中国国家自然科学基金;
关键词：
platinum-catalyzed; asymmetric catalysis; ring-opening reaction; oxabenzonorbornadiene; terminal alkyne; OXABICYCLIC ALKENES; AZABICYCLIC ALKENES; GRIGNARD-REAGENTS; BICYCLIC OLEFINS; COMPLEXES; NUCLEOPHILES; ALCOHOLS; HALIDES; ARYL; METATHESIS;
D O I：
10.1002/cjoc.201400174
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel platinum-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadiene with terminal alkynes is described. The reaction affords optically active cis-2-alkynyl-1,2-dihydronaphthalen-1-ols in moderate yields with good enantioselectivity in the presence of catalytic amounts of Pt(COD)Cl-2/(S)-BINAP and an excess of zinc powder. The products were obtained exclusively with the relative cis-configuration of the ring substituents and the prevalent (1R,2S)-configuration of the stereocenters, as determined by single crystal X-ray diffraction analysis.
引用
收藏
页码：613 / 618
页数：6
相关论文
共 39 条
  • [1] Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents
    Arrayás, RG
    Cabrera, S
    Carretero, JC
    [J]. ORGANIC LETTERS, 2003, 5 (08) : 1333 - 1336
  • [2] Enantioselective Ring Opening of meso-Epoxides with Aromatic Amines Catalyzed by Dinuclear Magnesium Complexes
    Bao, Hongli
    Wang, Zheng
    You, Tianpa
    Ding, Kuiling
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (01) : 67 - 71
  • [3] Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol
    Bertozzi, F
    Pineschi, M
    Macchia, F
    Arnold, LA
    Minnaard, AJ
    Feringa, BL
    [J]. ORGANIC LETTERS, 2002, 4 (16) : 2703 - 2705
  • [4] Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents
    Bos, Pieter H.
    Rudolph, Alena
    Perez, Manuel
    Fananas-Mastral, Martin
    Harutyunyan, Syuzanna R.
    Feringa, Ben L.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (12) : 1748 - 1750
  • [5] Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes
    Cabrera, S
    Arrayás, RG
    Carretero, JC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3944 - 3947
  • [6] Regioselective ring-opening metathesis-cross metathesis of bridgehead-substituted 7-azanorbornene
    Carreras, J.
    Avenoza, A.
    Busto, J. H.
    Peregrina, J. M.
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1235 - 1238
  • [7] Pd-catalyzed ring opening of oxa- and azabicyclic alkenes with aryl and vinyl halides: Efficient entry to 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols
    Chen, Chi-Li
    Martin, Stephen F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) : 4810 - 4817
  • [8] Palladium-Catalyzed Ring-Opening Reaction of Oxa/Azabenzonorbornadienes with Aryl Acetylenes
    Chen Hualei
    Li Sifeng
    Xu Jianbin
    Yang Qingjing
    Liu Shanshan
    Zhou Yongyun
    Huang Chao
    Fan Baomin
    [J]. ACTA CHIMICA SINICA, 2013, 71 (09) : 1243 - 1247
  • [9] Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Azabicyclic Alkenes
    Cheng, Hanchao
    Liang, Xiuli
    Li, Xiaolu
    Long, Yuhua
    Yang, Dingqiao
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (03) : 433 - 443
  • [10] Comparison of Ru- and Mo-based chiral olefin metathesis catalysts. Complementarity in asymmetric ring-opening/cross-metathesis reactions of oxa- and azabicycles
    Cortez, G. Alex
    Baxter, Carl A.
    Schrock, Richard R.
    Hoveyda, Amir H.
    [J]. ORGANIC LETTERS, 2007, 9 (15) : 2871 - 2874
1234