Enantioselective formal [2+2] cycloaddition of ketenes with nitroso compounds catalyzed by N-heterocyclic carbenes

被引：51
作者：
Wang, Tong [1 ]
Huang, Xue-Liang [1 ]
Ye, Song [1 ]
机构：
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 21期
基金：
美国国家科学基金会;
关键词：
HYDROXYCARBOXYLIC ACID-DERIVATIVES; ALPHA-KETOESTERS; BENZOIN CONDENSATION; ASYMMETRIC-SYNTHESIS; ALLYLIC ALKYLATION; ORGANOCATALYSIS; OXIDATION; KETONES;
D O I：
10.1039/c0ob00249f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [2+2] cycloaddition reaction of alkyl(aryl)ketenes and nitroso compounds to give the corresponding 1,2-oxazetidin-3-ones in moderate to good yields with high enantioselectivities. Reductive ring-opening of the oxazetidinones give the corresponding alpha-hydroxy acid derivatives in good yields.
引用
收藏
页码：5007 / 5011
页数：5
相关论文
共 43 条
  • [1] Aladro FJ, 2000, TETRAHEDRON LETT, V41, P3209
  • [2] Highly Enantioselective Benzoin Condensation Reactions Involving a Bifunctional Protic Pentafluorophenyl-Substituted Triazolium Precatalyst
    Baragwanath, Louise
    Rose, Christopher A.
    Zeitler, Kirsten
    Connon, Stephen J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) : 9214 - 9217
  • [3] Catalytic, enantioselective [4+2]-cycloadditions of ketene enolates and o-quinones:: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives
    Bekele, T
    Shah, MH
    Wolfer, J
    Abraham, CJ
    Weatherwax, A
    Lectka, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) : 1810 - 1811
  • [4] Copper-Catalyzed Enantioselective [2+2] Cycloadditions of 2-Nitrosopyridine with Ketenes
    Chatterjee, Indranil
    Jana, Chandan Kumar
    Steinmetz, Marc
    Grimme, Stefan
    Studer, Armido
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 945 - 948
  • [5] N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes
    Concellon, Carmen
    Duguet, Nicolas
    Smith, Andrew D.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 3001 - 3009
  • [6] Coppola G. M., 1997, A HYDROXY ACIDS ENAN
  • [7] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY LACTONES BY SHARPLESS ASYMMETRIC DIHYDROXYLATIONS OF KETENE ACETALS, ENOL ETHERS, AND ENE LACTONES
    CURRAN, DP
    KO, SB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6139 - 6141
  • [8] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES
    DAVIS, FA
    CHEN, BC
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 919 - 934
  • [9] Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives
    Dochnahl, Maximilian
    Fu, Gregory C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) : 2391 - 2393
  • [10] N-Heterocyclic carbene catalysed β-lactam synthesis
    Duguet, Nicolas
    Campbell, Craig D.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (06) : 1108 - 1113
12345