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 50 条
  • [1] Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes
    Chen, Xiang-Yu
    Ye, Song
    SYNLETT, 2013, 24 (13) : 1614 - 1622
  • [2] Enantioselective [2+2+2] cycloaddition of ketenes and carbon disulfide catalyzed by N-heterocyclic carbenes
    Wang, Xiao-Na
    Shen, Li-Tao
    Ye, Song
    CHEMICAL COMMUNICATIONS, 2011, 47 (29) : 8388 - 8390
  • [3] N-Heterocyclic Carbene Catalysis: Enantioselective Formal [2+2] Cycloaddition of Ketenes and N-Sulfinylanilines
    Jian, Teng-Yue
    He, Lin
    Tang, Cen
    Ye, Song
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9104 - 9107
  • [4] Formal cycloaddition of disubstituted ketenes with 2-oxoaldehydes catalyzed by chiral N-heterocyclic carbenes
    He, Lin
    Lv, Hui
    Zhang, Yan-Rong
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20): : 8101 - 8103
  • [5] Enantioselective [4+2] cycloaddition of ketenes and 1-azadienes catalyzed by N-heterocyclic carbenes
    Jian, Teng-Yue
    Shao, Pan-Lin
    Ye, Song
    CHEMICAL COMMUNICATIONS, 2011, 47 (08) : 2381 - 2383
  • [6] Enantioselective [4+2] cycloaddition of ketenes and 9,10-phenanthrenequinone catalyzed by N-heterocyclic carbenes
    Shao, Pan-Lin
    Chen, Xiang-Yu
    Sun, Li-Hui
    Ye, Song
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2316 - 2318
  • [7] [4+2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes
    Huang, Xue-Liang
    He, Lin
    Shao, Pan-Lin
    Ye, Song
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 192 - 195
  • [8] Theoretical understanding mechanisms and stereoselectivities of [2+2] cycloaddition of ketenes with ketimines catalyzed by bifunctional N-heterocyclic carbene
    Nan He
    Zhenhua Zhu
    Fangfang Li
    Yanyan Zhu
    Lingbo Qu
    Hongsheng Chen
    Structural Chemistry, 2020, 31 : 181 - 190
  • [9] Theoretical understanding mechanisms and stereoselectivities of [2+2] cycloaddition of ketenes with ketimines catalyzed by bifunctional N-heterocyclic carbene
    He, Nan
    Zhu, Zhenhua
    Li, Fangfang
    Zhu, Yanyan
    Qu, Lingbo
    Chen, Hongsheng
    STRUCTURAL CHEMISTRY, 2020, 31 (01) : 181 - 190
  • [10] DFT Investigation on Mechanisms and Stereoselectivities of [2+2+2] Multimolecular Cycloaddition of Ketenes and Carbon Disulfide Catalyzed by N-Heterocyclic Carbenes
    Zhang, Wen-Jing
    Wei, Dong-Hui
    Tang, Ming-Sheng
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23): : 11849 - 11859
12345