Regiospecific hydration of γ-hydroxy-α,β-acetylenic esters:: A novel asymmetric synthesis of tetronic acids

被引:65
|
作者
Rajaram, AR [1 ]
Pu, L [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
关键词
D O I
10.1021/ol060377v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The optically active gamma-hydroxy-alpha,beta-acetylenic esters are obtained from the enantioselective reaction of methyl propiolate with both aliphatic and aromatic aldehydes. These compounds can undergo regiospecific hydration in the presence of Zeise's dimer, [PtCl2(C2H4)](2), to generate the optically active tetronic acids.
引用
下载
收藏
页码:2019 / 2021
页数:3
相关论文
共 50 条
  • [21] Asymmetric, Organocatalytic, Three-Step Synthesis of γ-Hydroxy-(E)-α,β-Unsaturated Sulfones and Esters
    Petersen, Kimberly S.
    Posner, Gary H.
    ORGANIC LETTERS, 2008, 10 (20) : 4685 - 4687
  • [22] Characteristics of l-threonine transaldolase for asymmetric synthesis of β-hydroxy-α-amino acids
    Xu, Lian
    Wang, Li-Chao
    Xu, Xin-Qi
    Lin, Juan
    CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (21) : 5943 - 5952
  • [23] Cyclic acetal formation between 2-pyridinecarboxyaldehyde and γ-hydroxy-α,β-acetylenic esters
    Osman, Sami
    Koide, Kazunori
    TETRAHEDRON LETTERS, 2008, 49 (46) : 6550 - 6552
  • [24] Asymmetric synthesis of novel quaternary α-hydroxy-δ-lactam dipeptide surrogates.
    Semple, JE
    Reiner, JE
    Minami, NK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U995 - U996
  • [25] Synthesis of α-ketobutyrolactones and γ-hydroxy-α-keto acids
    Kang, HY
    Ji, YM
    Yu, YK
    Yu, JY
    Lee, Y
    Leet, SJ
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (12) : 1819 - 1826
  • [26] Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones
    Davies, Iwan R.
    Cheeseman, Matt
    Green, Rachel
    Mahon, Mary F.
    Merritt, Andrew
    Bull, Steven D.
    ORGANIC LETTERS, 2009, 11 (13) : 2896 - 2899
  • [27] Asymmetric synthesis of α-alkyl-α-hydroxy-γ-butyrolactones
    Pansare, SV
    Jain, RP
    Ravi, RG
    TETRAHEDRON-ASYMMETRY, 1999, 10 (16) : 3103 - 3106
  • [28] Novel threonine aldolases and their application to stereospecific synthesis of β-hydroxy-α-amino acids
    Kataoka, M
    Wada, M
    Ikemi, M
    Morikawa, T
    Miyoshi, T
    Shimizu, S
    ENZYME ENGINEERING XIV, 1998, 864 : 318 - 322
  • [29] Base-Catalyzed Highly Stereoselective Conversion of γ-Hydroxy-α,β-acetylenic Esters to γ-Acetoxy Dienoates
    Yue, Yang
    Yu, Xiao-Qi
    Pu, Lin
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (20) : 5104 - 5107
  • [30] Synthesis of New δ-(Polyfluoroalkyl)-δ-hydroxy-α-amino Acids
    Tolmacheva, Nataliya A.
    Gerus, Igor I.
    Dolovanyuk, Violetta G.
    Kondratov, Ivan S.
    Haufe, Guenter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (29) : 5012 - 5019