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

[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] Enol-Ugi Reaction for the Synthesis of Amino Acid Derived Coumarins
Neo, Ana G.
Castellano, Teresa G.
Marcos, Carlos F.
20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,
[3] Synthesis of novel chiral ligands from amino acids by the Ugi reaction
Dyker, G
Breitenstein, K
Henkel, G
TETRAHEDRON-ASYMMETRY, 2002, 13 (17) : 1929 - 1936
[4] 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
[5] 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
[6] 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
[7] 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
[8] Enol-Ugi Reaction of Hydroxycoumarins: Straightforward Synthesis of Amino Acid Derived Coumarin Enamines
Neo, Ana G.
Castellano, Teresa G.
Marcos, Carlos F.
SYNTHESIS-STUTTGART, 2015, 47 (16): : 2431 - 2438
[9] 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
[10] 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

← 1 2 3 4 5 →