Catalytic Nazarov Reaction of Aryl Vinyl Ketones via Binary Acid Strategy

被引：35
作者：
Xi, Zhi-Guo [1 ,2 ]
Zhu, Lihui [3 ]
Luo, Sanzhong [3 ]
Cheng, Jin-Pei [1 ,2 ]
机构：
[1] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 02期
关键词：
DIELS-ALDER REACTION; TERT-AMINOCYCLIZATION; EFFICIENT CATALYSIS; CYCLIZATION; DITERPENES;
D O I：
10.1021/jo302451b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe herein a viable binary acid strategy for the catalytic Nazarov reaction of aryl vinyl ketones. Simply combining a Lewis acid and a Bronsted acid led to a dramatic enhancement of the catalytic activity in the Nazarov reaction of aryl vinyl beta-ketoesters. The obtained optimal binary acid catalyst In(OTf)(3)/diphenyl phosphoric acid (DPP) can be applied to a range of aryl vinyl ketones with good activity. A trend of reactivity has also been summarized on the basis of mapping of the substituents.
引用
收藏
页码：606 / 613
页数：8
相关论文
共 43 条
  • [1] Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes
    Aggarwal, VK
    Beffield, AJ
    [J]. ORGANIC LETTERS, 2003, 5 (26) : 5075 - 5078
  • [2] First total synthesis of the 4a-methyltetrahydrofluorene diterpenoids (±)-dichroanal B and (±)-dichroanone
    Banerjee, M
    Mukhopadhyay, R
    Achari, B
    Banerjee, AK
    [J]. ORGANIC LETTERS, 2003, 5 (21) : 3931 - 3933
  • [3] A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization
    Canterbury, Daniel P.
    Herrick, Ildiko R.
    Um, Joann
    Houk, K. N.
    Frontier, Alison J.
    [J]. TETRAHEDRON, 2009, 65 (16) : 3165 - 3179
  • [4] Asymmetric Nazarov Reaction Catalyzed by Chiral Tris(oxazoline)/Copper(II)
    Cao, Peng
    Deng, Chao
    Zhou, You-Yun
    Sun, Xiu-Li
    Zheng, Jun-Cheng
    Xie, Zuowei
    Tang, Yong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) : 4463 - 4466
  • [5] Four new 6-Nor-5(6→7)abeo-abietane type diterpenes and antitumoral cytotoxic diterpene constituents from the bark of Taiwania cryptomerioides
    Chang, CI
    Chang, JY
    Kuo, CC
    Pan, WY
    Kuo, YH
    [J]. PLANTA MEDICA, 2005, 71 (01) : 72 - 76
  • [6] Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer
    Chen, Liujuan
    Zhang, Long
    Lv, Jian
    Cheng, Jin-Pei
    Luo, Sanzhong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 8891 - 8895
  • [7] Lewis base catalysis in organic synthesis
    Denmark, Scott E.
    Beutner, Gregory L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) : 1560 - 1638
  • [8] The Nazarov cyclization in organic synthesis. Recent advances
    Frontier, AJ
    Collison, C
    [J]. TETRAHEDRON, 2005, 61 (32) : 7577 - 7606
  • [9] Interrupting the Nazarov reaction: domino and cascade processes utilizing cyclopentenyl cations
    Grant, Tina N.
    Rieder, Curtis J.
    West, Frederick G.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (38) : 5676 - 5688
  • [10] Diterpenoids
    Hanson, JR
    [J]. NATURAL PRODUCT REPORTS, 2004, 21 (02) : 312 - 320
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