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
来源：
TETRAHEDRON LETTERS | 2025年 / 157卷
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
  • [41] Synthesis of functionalized pyroglutamic acids, part 1:: The synthetic utility of N-acylindole and the Ugi reaction with a chiral levulinic acid
    Buller, Matthew J.
    Gilley, Cynthla B.
    Nguyen, Brian
    Olshansky, Lisa
    Fraga, Breena
    Kobayashi, Yoshihisa
    SYNLETT, 2008, (15) : 2244 - 2248
  • [42] New Cytotoxic α-Aminoacylamide and bis-1,5-Disubstituted Tetrazole Adducts From Amino-Diterpene Molecules by Ugi Reaction
    Smirnova, Anna
    Tretyakova, Elena
    Kazakova, Oxana
    CHEMICAL BIOLOGY & DRUG DESIGN, 2024, 104 (03)
  • [43] Synthesis of Hydroxynaphthyl-Substituted α-Amino Acid Derivatives via a Modified Mannich Reaction
    Csuetoertoeki, Renata
    Szatmari, Istvan
    Mandi, Attila
    Kurtan, Tibor
    Fueloep, Ferenc
    SYNLETT, 2011, (13) : 1940 - 1946
  • [44] Application of the Heck reaction in the synthesis of macrocycles derived from amino alcohols
    Gibson, Susan E.
    Lecci, Cristina
    White, Andrew J. P.
    SYNLETT, 2006, (18) : 2929 - 2934
  • [45] Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles
    Vasconcelos, Stanley N. S.
    Fornari, Evelin
    Caracelli, Ignez
    Stefani, Helio A.
    MOLECULAR DIVERSITY, 2017, 21 (04) : 893 - 902
  • [46] Synthesis of bicyclic pyroglutamic acid featuring the Ugi reaction and a unique stereoisomerization at the angular position by Grob fragmentation followed by a transannular ketene [2+2] cycloaddition reaction
    Vamos, Mitchell
    Ozboya, Kerem
    Kobayashi, Yoshihisa
    SYNLETT, 2007, (10) : 1595 - 1599
  • [47] Stereocontrolled synthesis of anti-α-hydroxy-β-amino and anti-α,β-diamino acid derivatives by epoxidation of 1-arylthio-l-nitroalkenes
    Ambroise, L
    Dumez, E
    Szeki, A
    Jackson, RFW
    SYNTHESIS-STUTTGART, 2002, (15): : 2296 - 2308
  • [48] Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid Derived Nitriles
    Heikinheimo, Annakaisa
    Nieger, Martin
    Koskinen, Ari M. P.
    SYNLETT, 2023, 34 (12) : 1512 - 1518
  • [49] Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction
    Jousseaume, Thierry
    Wurz, Nathalie E.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1410 - 1414
  • [50] A convenient one-pot synthesis of novel tetraamides via 2-cyclopentylidenemalonic acid based Ugi-four component reaction
    Mokhtari, Tayebeh Sattaei
    Sheikhhosseini, Enayatollah
    Amrollahi, Mohammad Ali
    Sheibani, Hassan
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (03) : 300 - 305
12345