Efficient one-pot synthesis of enantiomerically pure N-protected-α-substituted piperazines from readily available α-amino acids

2018 ◽  
Vol 42 (3) ◽  
pp. 1595-1599 ◽  
Author(s):  
Mouhamad Jida ◽  
Steven Ballet
Keyword(s):  
Amino Acids ◽  
Protecting Group ◽  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83–92%), starting from commercially available N-protected amino acids.

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.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

ChemInform Abstract: One-Pot Synthesis of Enantiomerically Pure N-Protected Allylic Amines from N-Protected α-Amino Esters.

ChemInform ◽  
2016 ◽  
Vol 47 (36) ◽  
Author(s):  
Gaston Silveira-Dorta ◽  
Sergio J Alvarez-Mendez ◽  
Victor S Martin ◽  
Jose M Padron
Keyword(s):  
Allylic Amines ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Amino Esters ◽  
One Pot Synthesis

Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues

2016 ◽  
Vol 14 (44) ◽  
pp. 10473-10480 ◽  
Author(s):  
Sylvain Daunay ◽  
Remi Lebel ◽  
Laurence Farescour ◽  
Jean-Claude Yadan ◽  
Irene Erdelmeier
Keyword(s):  
Amino Acids ◽  
Protecting Group ◽  
One Pot ◽  
Step Procedure ◽  
Sulfur Containing

Natural and novel sulfur-containing amino acids are preparedviaa new regioselective one-pot two-step procedure.

One-Pot Synthesis of Sialo-Containing Glycosyl Amino Acids by Use of anN-Trichloroethoxycarbonyl-?-thiophenyl Sialoside

2005 ◽  
Vol 11 (3) ◽  
pp. 849-862 ◽  
Author(s):  
Hiroshi Tanaka ◽  
Masaatsu Adachi ◽  
Takashi Takahashi
Keyword(s):  
Amino Acids ◽  
One Pot ◽  
One Pot Synthesis

ChemInform Abstract: One-Pot Synthesis of Phenylseleno N-Acetyl α-Amino Acids: Supra-Molecular Self-Assembling in Organoselenium Compounds.

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
C. Parashiva Prabhu ◽  
Prasad P. Phadnis ◽  
Amey Wadawale ◽  
K. Indira Priyadarsini ◽  
Vimal K. Jain
Keyword(s):  
Amino Acids ◽  
Organoselenium Compounds ◽  
One Pot ◽  
One Pot Synthesis ◽  
Self Assembling

One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis

2011 ◽  
Vol 123 (6) ◽  
pp. 1429-1432 ◽  
Author(s):  
Tsuyoshi Mita ◽  
Jianyang Chen ◽  
Masumi Sugawara ◽  
Yoshihiro Sato
Keyword(s):  
Amino Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Alternative Method ◽  
Strecker Synthesis
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