Successively Recycle Waste as Catalyst: A One-Pot Wittig/1,4-Reduction/Paal-Knorr Sequence for Modular Synthesis of Substituted Furans

被引:65
作者
Chen, Long [1 ]
Du, Yi [2 ]
Zeng, Xing-Ping [1 ]
Shi, Tao-Da [1 ]
Zhou, Feng [1 ]
Zhou, Jian [1 ,3 ]
机构
[1] E China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Med, Xinhua Hosp, Shanghai 200092, Peoples R China
[3] Shanghai Inst Organ Chem, CAS, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
PHOSPHINE-INITIATED REACTIONS; PAAL-KNORR REACTION; BETA-AMINO ESTERS; O BOND FORMATION; POLYSUBSTITUTED FURANS; TETRASUBSTITUTED FURANS; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; (2-FURYL)CARBENE COMPLEXES;
D O I
10.1021/acs.orglett.5b00442
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.
引用
收藏
页码:1557 / 1560
页数:4
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共 86 条
  • [1] Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol
    Alaimo, Peter J.
    O'Brien, Robert
    Johnson, Adam W.
    Slauson, Sarah R.
    O'Brien, Jeannette M.
    Tyson, Elizabeth L.
    Marshall, Amanda-Lynn
    Ottinger, Colleen E.
    Chacon, Jon G.
    Wallace, Lorien
    Paulino, Corey Y.
    Connell, Sarah
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5111 - 5114
  • [2] Generation of α,β-Unsaturated Platinum Carbenes from Homopropargylic Alcohols: Rearrangements to Polysubstituted Furans
    Allegretti, Paul A.
    Ferreira, Eric M.
    [J]. ORGANIC LETTERS, 2011, 13 (21) : 5924 - 5927
  • [3] Green Chemistry: Principles and Practice
    Anastas, Paul
    Eghbali, Nicolas
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) : 301 - 312
  • [4] Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes
    Barluenga, Jose
    Riesgo, Lorena
    Vicente, Ruben
    Lopez, Luis A.
    Tomas, Miguel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13528 - +
  • [5] Bioinspired organocatalytic asymmetric reactions
    Bernardi, Luca
    Fochi, Mariafrancesca
    Franchini, Mauro Comes
    Ricci, Alfredo
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) : 2911 - 2922
  • [6] Developments in furan syntheses
    Brown, RCD
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) : 850 - 852
  • [7] Copper-Catalyzed C-O Bond Formation: An Efficient One-Pot Highly Regioselective Synthesis of Furans from (2-Furyl)Carbene Complexes
    Cao, Hua
    Zhan, Haiying
    Cen, Jinghe
    Lin, Jingxin
    Lin, Yuanguang
    Zhu, Qiuxia
    Fu, Minling
    Jiang, Huanfeng
    [J]. ORGANIC LETTERS, 2013, 15 (05) : 1080 - 1083
  • [8] Improving the Atom Efficiency of the Wittig Reaction by a "Waste as Catalyst/Co-catalyst" Strategy
    Cao, Jun-Jie
    Zhou, Feng
    Zhou, Jian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4976 - 4980
  • [9] Tandem and domino catalytic strategies for enantioselective synthesis
    Chapman, Christopher J.
    Frost, Christopher G.
    [J]. SYNTHESIS-STUTTGART, 2007, (01): : 1 - 21
  • [10] Diversified assembly of perfluoroalkyl-substituted furans and 2,5-dihydrofuran-2-ols
    Chen, Guofei
    He, Guangke
    Xue, Can
    Fu, Chunling
    Ma, Shengming
    [J]. TETRAHEDRON LETTERS, 2011, 52 (02) : 196 - 198