Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids

被引：25

作者：

Glotova, Tatyana E. ^{[1
]}

Dvorko, Marina Yu. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Chipanina, Nina N. ^{[1
]}

Kazheva, Olga N. ^{[2
]}

Chekhlov, Anatolii N. ^{[2
]}

Dyachenko, Oleg A. ^{[2
]}

Gusarova, Nina K. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia

来源：

TETRAHEDRON | 2009年 / 65卷 / 47期

关键词：

Amino acids; Acylacetylenes; N-Acylvinyl derivatives of amino acids; Nucleophilic addition; BETA-ENAMINONES; ONE-POT; COMPLEXES; CRYSTAL; CONDENSATION; HETEROCYCLES; CONVENIENT; KETONES; COPPER;

D O I：

10.1016/j.tet.2009.09.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot reaction of natural amino acids (glycine, beta-alanine, gamma-aminobutyric and epsilon-aminocapronic acids, D,L-valine, D,L-leucine, anthranilic acid) with bielectrophilic acylacetylenes proceeds chemo-, regio- and stereospecifically in the presence of NaOH (45-50 degrees C, 4 h, EtCH-H2O) to give (after treatment of the reaction mixture with aqueous HCl) Z-isomers of N-acylvinylderivatives of amino acids in 87-94% yield. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：9814 / 9818

页数：5

共 50 条

[21] Regio- and Diastereoselective Decarboxylative Allylation of N-Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis
Zheng, Jun
Nopper, Christoph
Bibi, Rifhat
Nikbakht, Ali
Bauer, Felix
Breit, Bernhard
ACS CATALYSIS, 2022, 12 (10) : 5949 - 5960
[22] A practical synthesis of α-amino ketones via aryllithium addition to N-boc-α-amino acids
Florjancic, AS
Sheppard, GS
SYNTHESIS-STUTTGART, 2003, (11): : 1653 - 1656
[23] Synthesis of new 5-N-pyrazolyl amino acids, pyrazolopyrimidines and pyrazolopyridines derivatives
Shalaby, AM
Fathalla, OA
Kassem, EMM
Zaki, MEA
ACTA CHIMICA SLOVENICA, 2000, 47 (02) : 187 - 203
[24] Straightforward synthesis of fluorinated amino acids by Michael addition of ethyl bromodifluoroacetate to α,β-unsaturated α-amino acid derivatives
Kondratov, Ivan S.
Bugera, Maxym Ya.
Tolmachova, Nataliya A.
Daniliuc, Constantin G.
Haufe, Guenter
JOURNAL OF FLUORINE CHEMISTRY, 2018, 211 : 100 - 108
[25] SYNTHESIS OF N-ALKYLDIMETHYL DERIVATIVES OF OMEGA-AMINO ACIDS
SWAIN, AP
BRAUN, DF
NAEGELE, SK
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (09): : 1087 - 1091
[26] Synthesis and characterization of N-retinylidene derivatives of polar amino acids
Pshenichnikova, AB
Karnaukhova, EN
Mitsner, BI
Shvets, VI
BIOORGANICHESKAYA KHIMIYA, 1996, 22 (10-11): : 852 - 855
[27] Schiff base and reductive amination reactions of -amino acids: a facile route toward N-alkylated amino acids and peptoid synthesis
Fu, Xiaohui
Li, Zheng
Wei, Jirui
Sun, Jing
Li, Zhibo
POLYMER CHEMISTRY, 2018, 9 (37) : 4617 - 4624
[28] Stereospecific synthesis of new 4-amino-1,2,3-cyclohexanetricarboxylic acids and 4-amino-1,3-cyclohexanedicarboxylic acids
Arakawa, Y
Tajima, M
Arakawa, Y
Yoshifuji, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (01) : 81 - 85
[29] Facile Synthesis of Nα-Protected Amino/Peptide Hydroxamic Acids Mediated by COMU
Nageswara Rao Panguluri
Vommina V. Basavaprabhu
International Journal of Peptide Research and Therapeutics, 2014, 20 : 377 - 384
[30] A Facile Synthesis of N-Phosphoryl Amino Acids Containing Hydroxy Group
Jian Chen ZHANG
Chinese Chemical Letters, 2004, (06) : 646 - 648

← 1 2 3 4 5 →