Metal-free, direct conversion of α-amino acids into α-keto γ-amino esters for the synthesis of α,γ-peptides

2017 ◽  
Vol 15 (37) ◽  
pp. 7736-7742 ◽  
Author(s):  
D. Hernández ◽  
A. Boto ◽  
D. Guzmán ◽  
E. Alvarez
Keyword(s):  
Amino Acids ◽  
Direct Conversion ◽  
Reaction Intermediates ◽  
Metal Free ◽  
Amino Esters

An efficient, metal-free synthesis of unusual α-keto γ-amino esters from α-amino acids is achieved by a radical scission–oxidation–addition of silyloxy acrylates procedure, where no purification of the reaction intermediates is needed. The process allows the synthesis of α,γ-peptides.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones

2016 ◽  
Vol 52 (14) ◽  
pp. 2885-2888 ◽  
Author(s):  
Joice Thomas ◽  
Sampad Jana ◽  
Jubi John ◽  
Sandra Liekens ◽  
Wim Dehaen
Keyword(s):  
Natural Products ◽  
Primary Amines ◽  
Metal Free ◽  
Amino Esters

A metal-free route towards different 1,2,3-triazole heterocycles was accomplished by using inexpensive and readily available ketones and primary amines. This reaction is very general and was extended to functionalize different amino esters, dendrimers and natural products.

Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions

2016 ◽  
Vol 18 (9) ◽  
pp. 2244-2247 ◽  
Author(s):  
Patrick S. Fier ◽  
Kevin M. Maloney
Keyword(s):  
Transition Metal ◽  
Direct Conversion ◽  
Metal Free

scholarly journals Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters

2018 ◽  
Vol 16 (17) ◽  
pp. 3168-3176 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Sampad Jana ◽  
Lucie Borkova ◽  
Joice Thomas ◽  
Wim Dehaen
Keyword(s):  
Amino Acids ◽  
Enantiomerically Pure ◽  
Triazole Derivatives ◽  
Amino Esters ◽  
Good Yielding ◽  
Derivatives Of

An easy, good-yielding access to functionalized enantiomerically pure 1,2,3-triazole derivatives of amino acids using commercially available ketones and amino esters is described.

scholarly journals The synthesis of imidazo[1,5-a]quinolinesviaa decarboxylative cyclization under metal-free conditions

RSC Advances ◽  
2018 ◽  
Vol 8 (41) ◽  
pp. 23058-23065 ◽  
Author(s):  
Zicong Yan ◽  
Changfeng Wan ◽  
Yu Yang ◽  
Zhenggen Zha ◽  
Zhiyong Wang
Keyword(s):  
Amino Acids ◽  
Metal Free ◽  
Decarboxylative Cyclization

An iodine-mediated decarboxylative cyclization was developed from α-amino acids and 2-methyl quinolines under metal-free conditions, affording a variety of imidazo[1,5-a]quinolines with moderate to good yields.

scholarly journals Morpholin-2-one Derivatives via Intramolecular Acid-Catalyzed Hydroamination

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1643-1648 ◽  
Author(s):  
David Knight ◽  
Thomas Wirth ◽  
Abdul Hadi Aldmairi
Keyword(s):  
Amino Acids ◽  
Catalytic Amount ◽  
Practical Method ◽  
Trifluoromethanesulfonic Acid ◽  
Reaction Conditions ◽  
Available N ◽  
Metal Free ◽  
Acid Catalyzed

Substituted morpholin-2-one derivatives were readily obtained in two steps starting from commercially available N-protected amino acids. In a metal-free and practical method, a catalytic amount of trifluoromethanesulfonic acid was sufficient to generate morpholinones under mild reaction conditions in an intramolecular hydroamination reaction in good to excellent yields.

Transition Metal‐Free, Base‐Induced Arylation of Amino Acids: Synthesis of N ‐( para ‐Substituted phenyl)amino‐2‐carboxylic acids

2020 ◽  
Vol 5 (28) ◽  
pp. 8644-8648 ◽  
Author(s):  
Adejoke D. Osinubi ◽  
Josephat U. Izunobi ◽  
Olayinka T. Asekun ◽  
Oluwole B. Familoni ◽  
Xiaoguang Bao
Keyword(s):  
Amino Acids ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Free Base ◽  
Metal Free

Convenient Synthesis of Furo[3,2-b]quinolin-4(1H)-ones

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 911-915
Author(s):  
Veronika Králová ◽  
Miroslav Soural ◽  
Radim Horák ◽  
Pavel Hradil
Keyword(s):  
Methanesulfonic Acid ◽  
Starting Material ◽  
Simple Synthesis ◽  
Reaction Intermediates ◽  
Metal Free ◽  
Convenient Synthesis

In this work, we report the simple synthesis of furo[3,2-b]quinolin-4(1H)-ones from readily available 4-ethynyl-[1,3]dioxolo[4,5-c]quinolone as the key starting material. After Sonogashira (hetero)arylation, formation of the furoquinoline scaffold was accomplished using methanesulfonic acid and metal-free conditions. Although the cyclization was affected by the substitution of reaction intermediates, the method allowed the preparation of derivatives varying at the C3-position.

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