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 One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

2016 ◽  
Vol 12 ◽  
pp. 957-962 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Sergio J Álvarez-Méndez ◽  
Víctor S Martín ◽  
José M Padrón
Keyword(s):  
Amino Acids ◽  
Allylic Amines ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Amino Esters ◽  
One Pot Synthesis ◽  
Sequential Reduction ◽  
Natural Amino Acids ◽  
Hydroxy Groups

An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected α-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction–olefination process. The sequential reduction with DIBAL-H at −78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate the intermediate aldehyde. This circumvents the problem of instability of the aldehydes. The method tolerates well both Wittig and Horner–Wadsworth–Emmons organophosphorus reagents. A better Z-(dia)stereoselectivity was observed when compared to the previous one-pot method. The (dia)stereoselectivity of the process was affected neither by the reaction solvent nor by the amount of DIBAL-H employed. The method is compatible with the presence of free hydroxy groups as shown with serine and threonine derivatives.

scholarly journals Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
Juan I. Sarmiento-Sánchez ◽  
Adrián Ochoa-Terán ◽  
Ignacio A. Rivero
Keyword(s):  
Amino Acids ◽  
Combinatorial Library ◽  
Structural Characteristics ◽  
Experimental Conditions ◽  
Enantiomerically Pure ◽  
Amino Esters ◽  
Dpph Method ◽  
Antioxidant Evaluation ◽  
Specific Reactivity

The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters6are reported in good yields from anin situgeneratedα-azidomethyl ketone. Optimum experimental conditions were established for preparation ofα-halomethyl ketones10andα-N,N-dipropargylamino esters11, all derived fromα-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds6was assayed by DPPH method. The compound6cwith an IC50of 75.57 ± 1.74 μg mL−1was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modifiedα-amino acids employed in the synthesis.

scholarly journals (R)-α-Aminoadipic Acid: A Versatile Precursor for the Synthesis of D-Amino Acids

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Amina Sadiq ◽  
Norbert Sewald
Keyword(s):  
Amino Acids ◽  
Building Block ◽  
Large Scale ◽  
Starting Material ◽  
Pipecolic Acid ◽  
Cephalosporin C ◽  
Enzymatic Cleavage ◽  
Enantiomerically Pure ◽  
Unusual Amino Acids ◽  
Derivatives Of

The ready accessibility of (R)-α-aminoadipic acid by enzymatic cleavage of cephalosporin C (CephC) in the production of 7-aminocephalosporanic acid (7-ACA) on a large scale makes it a favorable chiral pool building block for the synthesis of unusual amino acids. A route for the synthesis of C-5-alkenyl and C-6-alkylidene derivatives of (R)-pipecolic acid is described which utilizes (R)-α-aminoadipic acid as the enantiomerically pure starting material. Moreover, the synthesis of azido and triazolyl derivatives of (R)-α-aminoadipic acid is reported.

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>

scholarly journals Enzymatic Approach to the Synthesis of Enantiomerically Pure Hydroxy Derivatives of 1,3,5-Triaza-7-phosphaadamantane

2021 ◽  
Author(s):  
Małgorzata Kwiatkowska ◽  
Jarosław Błaszczyk ◽  
Lesław Sieroń ◽  
Piotr Kiełbasiński
Keyword(s):  
Enantiomerically Pure ◽  
Derivatives Of

Derivatives of aminoquinones with N-protected amino acids

1998 ◽  
Vol 5 (4) ◽  
pp. 259-262 ◽  
Author(s):  
Chrysostomos Pachatouridis ◽  
Elias A. Couladouros ◽  
Vassilios P. Papageorgiou ◽  
Maria Liakopoulou-Kyriakides
Keyword(s):  
Amino Acids ◽  
Derivatives Of
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