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

[11] 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
[12] Synthesis of a chiral β-amino acid derivative by a cobalt-catalysed coupling reaction
Pan, Xianhua
Yu, Wansheng
Ou, Wenhua
Tao, Xiaohu
Wan, Jiaomei
Liu, Feng
JOURNAL OF CHEMICAL RESEARCH, 2011, (09) : 545 - 546
[13] Ugi Reaction of Amino Acids: From Facile Synthesis of Polypeptoids to Sequence-Defined Macromolecules
Tao, Yue
Tao, Youhua
MACROMOLECULAR RAPID COMMUNICATIONS, 2021, 42 (06)
[14] 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
[15] ASYMMETRIC INDUCTION DURING SYNTHESIS OF AMINO ACIDS BY PASSERINI-UGI REACTION
HERLINGER, H
RUCKER, D
KLEIMANN, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (12) : 808 - +
[16] Application of isocyanides derived from α-amino acids as substrates for the Ugi reaction
Berlozecki, Stanislaw
Szymanski, Wiktor
Ostaszewski, Ryszard
SYNTHETIC COMMUNICATIONS, 2008, 38 (16) : 2714 - 2721
[17] Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives
Ouchakour, Lamiaa
Abrahami, Renata A.
Forro, Eniko
Haukka, Matti
Fulop, Ferenc
Kiss, Lorand
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (12) : 2202 - 2211
[18] AMINO ACID SYNTHESIS BY REVERSAL OF THE AMINO ACID OXIDASE REACTION
RADHAKRISHNAN, AN
MEISTER, A
JOURNAL OF BIOLOGICAL CHEMISTRY, 1958, 233 (02) : 444 - 450
[19] Highly stereocontrolled synthesis of amino alcohols and amino sugars from organoboronic acids
Petasis, NA
Zavialov, IA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U51 - U51
[20] Efficient Synthesis Of Arrays Of Amino Acid Derived Ugi Products With Subsequent Amidation
Wang, Wei
Doemling, Alexander
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03): : 403 - 409

← 1 2 3 4 5 →