Highly enantioselective synthesis of a fluorescent amino acid

被引:16
|
作者
Kele, P
Sui, GD
Huo, Q
Leblanc, RM
机构
[1] Univ Miami, Ctr Supramol Sci, Coral Gables, FL 33124 USA
[2] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA
关键词
D O I
10.1016/S0957-4166(00)00459-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A high enantiomeric excess (>99.5%) synthesis of L- 2-amino-3-(7-methoxy-4-coumaryl) propionic acid (L-Amp) is described. The two step synthesis route of this non-proteinogenic amino acid includes an oxazinone derivative as glycine enolate, which is alkylated with the fluorogenic group. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:4959 / 4963
页数:5
相关论文
共 50 条
  • [31] Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
    Xu, Shiqing
    Oda, Akimichi
    Bobinski, Thomas
    Li, Haijun
    Matsueda, Yohei
    Negishi, Ei-ichi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (32) : 9319 - 9322
  • [32] Pressure dependent highly enantioselective hydrogenation of unsaturated β-amino acid precursors
    Heller, D
    Holz, J
    Drexler, HJ
    Lang, J
    Drauz, K
    Krimmer, HP
    Börner, A
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20): : 6816 - 6817
  • [33] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives
    Córdova, A
    Watanabe, S
    Tanaka, F
    Notz, W
    Barbas, CF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1866 - 1867
  • [34] A highly enantioselective chiral Schiff-base fluorescent sensor for mandelic acid
    Dhara, Koushik
    Sarkar, Krishanu
    Roy, Partha
    Nandi, Mahasweta
    Bhaumik, Asim
    Banerjee, Pradyot
    TETRAHEDRON, 2008, 64 (14) : 3153 - 3159
  • [35] Highly enantioselective fluorescent recognition of mandelic acid derivatives by chiral salen macrocycles
    Tanaka, Koichi
    Tsuchitani, Takeshi
    Fukuda, Noriaki
    Masumoto, Asuka
    Arakawa, Ryuichi
    TETRAHEDRON-ASYMMETRY, 2012, 23 (3-4) : 205 - 208
  • [36] Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes
    Ibrahem, I
    Córdova, A
    TETRAHEDRON LETTERS, 2005, 46 (16) : 2839 - 2843
  • [37] Catalytic, enantioselective alkylation of α-amino esters:: The synthesis of nonnatural α-amino acid derivatives
    Ferraris, D
    Young, B
    Cox, C
    Dudding, T
    Drury, WJ
    Ryzhkov, L
    Taggi, AE
    Lectka, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) : 67 - 77
  • [38] Enantioselective solid-phase synthesis of α-amino acid derivatives
    O'Donnell, MJ
    Delgado, F
    Pottorf, RS
    TETRAHEDRON, 1999, 55 (20) : 6347 - 6362
  • [39] Organocatalytic Enantioselective Synthesis of α-Fluoro-β-amino Acid Derivatives
    Straub, Matthew R.
    Birman, Vladimir B.
    ORGANIC LETTERS, 2018, 20 (23) : 7550 - 7553
  • [40] Biomimetic enantioselective synthesis of β,β-difluoro-α-amino acid derivatives
    Peng, Qiupeng
    Yan, Bingjia
    Li, Fangyi
    Lang, Ming
    Zhang, Bei
    Guo, Donghui
    Bierer, Donald
    Wan, Jian
    COMMUNICATIONS CHEMISTRY, 2021, 4 (01)