Stereocontrolled synthesis of an α-monosubstituted α-amino acid derivative from a Ugi reaction product

被引:0
|
作者
Tsukamoto, Shuntaro [1 ]
Suzuki, Yuki [1 ]
Oikawa, Masato [1 ]
机构
[1] Yokohama City Univ, Seto 22?2 Kanazawa Ku, Yokohama 2360027, Japan
关键词
alpha-amino acid; Ugi reaction; Chiral morpholinone; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASSIGNMENT;
D O I
10.1016/j.tetlet.2025.155488
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein an unprecedented concept for an enantiospecific synthetic strategy for alpha-amino acid derivatives starting from Ugi four-component coupling reaction employing chiral amine, via a chiral morpholinone intermediate. This concept was proven by the successful synthesis of (S)-N-Ac-tert-leucine.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Development of a stereoselective Ugi reaction starting from an oxanorbornene β-amino acid derivative
    Banfi, Luca
    Basso, Andrea
    Chiappe, Cinzia
    De Moliner, Fabio
    Riva, Renata
    Sonaglia, Lorenzo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (19) : 3819 - 3829
  • [2] Synthesis of quaternary α-amino acid-based arginase inhibitors via the Ugi reaction
    Golebiowski, Adam
    Whitehouse, Darren
    Beckett, R. Paul
    Van Zandt, Michael
    Ji, Min Koo
    Ryder, Todd R.
    Jagdmann, Erik
    Andreoli, Monica
    Lee, Yung
    Sheeler, Ryan
    Conway, Bruce
    Olczak, Jacek
    Mazur, Marzena
    Czestkowski, Wojciech
    Piotrowska, Wieslawa
    Cousido-Siah, Alexandra
    Ruiz, Francesc X.
    Mitschler, Andre
    Podjarny, Alberto
    Schroeter, Hagen
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (17) : 4837 - 4841
  • [3] Synthesis of alginate derivative via the Ugi reaction and its characterization
    Yan, Huiqiong
    Chen, Xiuqiong
    Li, Jiacheng
    Feng, Yuhong
    Shi, Zaifeng
    Wang, Xianghui
    Lin, Qiang
    CARBOHYDRATE POLYMERS, 2016, 136 : 757 - 763
  • [4] The synthesis of a chiral β-amino acid derivative by the Grignard reaction of an aspartic acid equivalent
    Liu, Feng
    Yu, Wansheng
    Ou, Wenhua
    Xu, Xiaojiong
    Ruan, Libo
    Wang, Xiaoke
    Li, Yiming
    Peng, Xijiang
    Tao, Xiaohu
    Mao, Jun
    Wan, Jiaomei
    Pan, Xianhua
    JOURNAL OF CHEMICAL RESEARCH, 2010, (09) : 517 - 519
  • [5] Synthesis of Proteasome Inhibitor Omuralide Featuring Stereocontrolled Ugi Reaction and Novel Convertible Isocyanide
    Gilley, Cynthia B.
    Buller, Matthew J.
    Kobayashi, Yoshihisa
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2009, 67 (11) : 1183 - 1193
  • [6] Long-Range Diastereoselectivity in an Ugi Reaction: Stereocontrolled and Diversity-Oriented Synthesis of Tetrahydrobenzoxazepines
    Banfi, Luca
    Bagno, Alessandro
    Basso, Andrea
    De Santis, Carlo
    Riva, Renata
    Rastrelli, Federico
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5064 - 5075
  • [7] Organocatalytic Synthesis of α,α-Diaryl Substituted α-Amino Acid Derivatives by an Interrupted Three-Component Ugi Reaction
    Glavac, Danijel
    Jeric, Ivanka
    Gredicak, Matija
    CROATICA CHEMICA ACTA, 2019, 92 (02) : 203 - 209
  • [8] The Ugi reaction with CF3-carbonyl compounds: effective synthesis of α-trifluoromethyl amino acid derivatives
    Gulevich, Anton V.
    Shevchenko, Nikolay E.
    Balenkova, Elisabeth S.
    Roeschenthaler, Gerd-Volker
    Nenajdenko, Valentine G.
    TETRAHEDRON, 2008, 64 (51) : 11706 - 11712
  • [9] Stereocontrolled Synthesis of β-Amino Alcohols from Lithiated Aziridines and Boronic Esters
    Schmidt, Frank
    Keller, Florian
    Vedrenne, Emeline
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (06) : 1149 - 1152
  • [10] Concise Synthesis of Non-Protein Amino Acid from Natural Product via Schmidt Reaction
    Gajcy, Kamila
    Librowski, Tadeusz
    Lochynski, Stanislaw
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (03) : 186 - 188