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

页数：4

共 50 条

[31] Stereocontrolled synthesis of all four stereoisomers of fully protected 2-amino-3-hydroxypentanoic acid from imines derived from D-glyceraldehyde
Badorrey, R
Cativiela, C
Díaz-de-Villegas, MD
Gálvez, JA
TETRAHEDRON, 1999, 55 (49) : 14145 - 14160
[32] Highly Stereocontrolled Total Synthesis of β-D-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis
Li, Nan-Sheng
Scharf, Louise
Adams, Erin J.
Piccirilli, Joseph A.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12) : 5970 - 5986
[33] Synthesis of conformationally constrained tricyclic β-lactam enantiomers through Ugi four-center three-component reactions of a monoterpene-based β-amino acid
Szakonyi, Zsolt
Sillanpaa, Reijo
Fueloep, Ferenc
MOLECULAR DIVERSITY, 2010, 14 (01) : 59 - 65
[34] Oxidative cross-coupling reaction by scandium catalysis for synthesis of α-alkyl α-amino acid ester derivatives
Wei, Xiao-Hong
Zhao, Lian-Biao
Zhou, Han-Cheng
RSC ADVANCES, 2017, 7 (27): : 16561 - 16564
[35] A novel route to racemic and nonracemic products of the Ugi reaction: Synthesis of Ugi's labile alpha-adducts from iminoaziridines and carboxylic acids, and their transformations
Quast, H
Aldenkortt, S
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (04) : 462 - 469
[36] Stereocontrolled Synthesis of Difunctionalized Azetidinones and 2,3-Amino Acid Derivatives from Cyclodienes by Ring-Opening and Cross-Metathesis Reactions
Kardos, MaRton
Kiss, Lorand
Fueloep, Ferenc
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1155 - 1159
[37] CuI/RhII-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters
Jung, Da Jung
Jeon, Hyun Ji
Lee, Joo Hyun
Lee, Sang-gi
ORGANIC LETTERS, 2015, 17 (14) : 3498 - 3501
[38] A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction
Gassa, Federico
Contini, Alessandro
Fontana, Gabriele
Pellegrino, Sara
Gelmi, Maria Luisa
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) : 7099 - 7106
[39] SINGLE-STEP SYNTHESIS OF RACEMIC DIPEPTIDES AND TRIPEPTIDES DERIVED FROM UNNATURAL BETA-HYDROXY AND BETA-MERCAPTO ALPHA-AMINO-ACIDS BY THE UGI REACTION
HATAM, M
TEHRANFAR, D
MARTENS, J
SYNTHESIS-STUTTGART, 1994, (06): : 619 - 623
[40] A novel synthesis, including asymmetric synthesis, of α-quarternary α-amino acid methyl esters from ketones via sulfinyloxiranes
Satoh, T
Hirano, M
Kuroiwa, A
TETRAHEDRON LETTERS, 2005, 46 (15) : 2659 - 2662

← 1 2 3 4 5 →