Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-D-xylopyranosylamine

2001 ◽  
Vol 79 (12) ◽  
pp. 1934-1939 ◽  
Author(s):  
Günther Ross ◽  
Ivar Ugi
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Chiral Amine ◽  
Peptide Derivatives ◽  
Stereoselective Syntheses

Since 1961, the synthesis of α-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these α-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-β-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.Key words: stereoselective U-4CR, chiral amine component, amino carbohydrate, α-amino acid derivatives.

One-pot synthesis of β-amino acid derivatives from α-amino acids

2006 ◽  
Vol 47 (49) ◽  
pp. 8757-8760 ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernández ◽  
Alicia Boto ◽  
Eleuterio Álvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis

One-Pot Synthesis of β-Amino Acid Derivatives from α-Amino Acids.

ChemInform ◽  
2007 ◽  
Vol 38 (13) ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernandez ◽  
Alicia Boto ◽  
Eleuterio Alvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

2011 ◽  
Vol 7 ◽  
pp. 1570-1576 ◽  
Author(s):  
Elizabeth P Jones ◽  
Peter Jones ◽  
Andrew J P White ◽  
Anthony G M Barrett
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Aryl Group ◽  
Hydrolysis Of

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

scholarly journals Stereodivergent entry to β-branched β-trifluoromethyl α-amino acid derivatives by sequential catalytic asymmetric reactions

2021 ◽  
Author(s):  
Vasco Corti ◽  
Riccardo Riccioli ◽  
Ada Martinelli ◽  
Sofia Sandri ◽  
Mariafrancesca Fochi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Reactions ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

Currently, conventional reductive catalytic methodologies do not guarantee general access to enantioenriched β-branched β-trifluoromethyl α-amino acid derivatives. Herein, a one-pot approach to these important α-amino acids, grounded on the reduction...

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

2005 ◽  
Vol 58 (11) ◽  
pp. 778 ◽  
Author(s):  
Andrew B. Hughes ◽  
Brad E. Sleebs
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reductive Cleavage ◽  
High Yield ◽  
Amino Acid Derivatives ◽  
Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

2018 ◽  
Vol 16 (37) ◽  
pp. 8311-8317 ◽  
Author(s):  
Zhongxiang Chen ◽  
Hongjun Fan ◽  
Shiwei Yang ◽  
Guangling Bian ◽  
Ling Song
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
The Absolute

Two simple 1H NMR tests give the absolute configurations of α-amino acids.

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