scholarly journals In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters

2017 ◽  
Vol 82 (16) ◽  
pp. 8514-8526 ◽  
Author(s):  
Shyam S. Samanta ◽  
Stéphane P. Roche
Keyword(s):  
One Pot ◽  
Amino Esters ◽  
One Pot Synthesis

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.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

One-Pot Synthesis of ABC Type Triblock Copolymers via in situ Click [3 + 2] and Diels−Alder [4 + 2] Reactions

2007 ◽  
Vol 40 (2) ◽  
pp. 191-198 ◽  
Author(s):  
Hakan Durmaz ◽  
Aydan Dag ◽  
Ozcan Altintas ◽  
Tuba Erdogan ◽  
Gurkan Hizal ◽  
...  
Keyword(s):  
Triblock Copolymers ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis

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

Facile one-pot synthesis of 2-amino-1,3,4-oxadiazole tethered peptidomimetics by molecular-iodine-mediated cyclodeselenization

2017 ◽  
Vol 41 (19) ◽  
pp. 11225-11229 ◽  
Author(s):  
L. Santhosh ◽  
C. Srinivasulu ◽  
S. Durgamma ◽  
Girish Prabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Molecular Iodine ◽  
One Pot ◽  
Highly Efficient ◽  
One Pot Synthesis

Mild and highly efficient I2 and Et3N aided cyclodeselenization of in situ generated selenosemicarbazide is described to obtain 2-amino-1,3,4-oxadiazole peptidomimetics.

Palladium-Catalyzed One-Pot Synthesis of C2-Quaternary Indolin-3-ones via 1H -indole-3-sulfonates Generated in Situ from 2-Alkynyl Arylazides and Sulfonic Acids

2017 ◽  
Vol 359 (23) ◽  
pp. 4147-4152 ◽  
Author(s):  
Xiaoxiang Zhang ◽  
Ping Li ◽  
Chang Lyu ◽  
Wanxiong Yong ◽  
Jing Li ◽  
...  
Keyword(s):  
Sulfonic Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed
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