Phosphine-Catalyzed Tandem Reaction of Allenoates with Nitroalkenes

被引：65
作者：
Guan, Xiao-Yang [1 ]
Wei, Yin [1 ]
Shi, Min [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 21期
基金：
中国国家自然科学基金;
关键词：
BAYLIS-HILLMAN REACTION; N-SULFONATED IMINES; ENANTIOSELECTIVE 3+2 ANNULATIONS; ELECTRON-DEFICIENT OLEFINS; FUNCTIONALIZED CYCLOPENTENES; ALLENIC ESTERS; CYCLOADDITION REACTIONS; ACTIVATED OLEFINS; GLUTAMATE ANALOGS; 2,3-BUTADIENOATES;
D O I：
10.1021/ol102191p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A P(p-FC6H4)(3)-catalyzed tandem reaction between ethyl 2,3-butadienoate and nitroalkenes has been developed, which involves a [3 + 2] cycloaddition and a subsequent umpolung addition. The asymmetric version of this tandem reaction has also been investigated by using chiral phosphanes.
引用
收藏
页码：5024 / 5027
页数：4
相关论文
共 52 条
  • [1] Small-molecule inhibitors of protein geranylgeranyltransferase type I
    Castellano, Sabrina
    Fiji, Hannah D. G.
    Kinderman, Sape S.
    Watanabe, Masaru
    de Leon, Pablo
    Tamanoi, Fuyuhiko
    Kwon, Ohyun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) : 5843 - +
  • [2] Phosphine-mediated [4+2] annulation of bis(enones):: A Lewis base catalyzed "mock Diels-Alder" reaction
    Couturier, M
    Ménard, F
    Ragan, JA
    Riou, M
    Dauphin, E
    Andresen, BM
    Ghosh, A
    Dupont-Gaudet, K
    Girardin, M
    [J]. ORGANIC LETTERS, 2004, 6 (11) : 1857 - 1860
  • [3] Enantioselective catalysis and complexity generation from allenoates
    Cowen, Bryan J.
    Miller, Scott J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3102 - 3116
  • [4] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
    Du, YS
    Lu, XY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) : 6463 - 6465
  • [5] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition
    Du, YS
    Lu, XY
    Yu, YH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) : 8901 - 8905
  • [6] Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes
    Dudding, Travis
    Kwon, Ohyun
    Mercier, Evan
    [J]. ORGANIC LETTERS, 2006, 8 (17) : 3643 - 3646
  • [7] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions
    Fang, Yuan-Qing
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5660 - +
  • [8] Screening of chiral phosphines as catalysts for the enantioselective [3+2] annulations of N-tosylimines with allenic esters
    Fleury-Bregeot, Nicolas
    Jean, Ludovic
    Retailleau, Pascal
    Marinetti, Angela
    [J]. TETRAHEDRON, 2007, 63 (48) : 11920 - 11927
  • [9] The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts
    Frank, SA
    Mergott, DJ
    Roush, WR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2404 - 2405
  • [10] Chiral sterically congested phosphane-amide bifunctional organocatalysts in asymmetric aza-Morita-Baylis-Hillman reactions of N-sulfonated imines with methyl and ethyl vinyl ketones
    Guan, Xiao-Yang
    Jiang, Ying-Qing
    Shi, Min
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) : 2150 - 2155
123456