Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis

ChemCatChem ◽  
2017 ◽  
Vol 9 (4) ◽  
pp. 555-558 ◽  
Author(s):  
Florian Uthoff ◽  
Hirofumi Sato ◽  
Harald Gröger
Keyword(s):  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis

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

One-Pot Synthesis of Novel Enantiomerically Pure and Racemic 4-Ferrocenyl-β-lactams and Their Reactivity in Acidic Media

2005 ◽  
Vol 2005 (15) ◽  
pp. 3326-3333 ◽  
Author(s):  
Luca Bernardi ◽  
Bianca F. Bonini ◽  
Mauro Comes-Franchini ◽  
Gabriella Dessole ◽  
Mariafrancesca Fochi ◽  
...  
Keyword(s):  
Acidic Media ◽  
One Pot ◽  
Enantiomerically Pure ◽  
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.

scholarly journals Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60

2014 ◽  
Vol 10 ◽  
pp. 1308-1316 ◽  
Author(s):  
Marco Caricato ◽  
Silvia Díez González ◽  
Idoia Arandia Ariño ◽  
Dario Pasini
Keyword(s):  
Dicarboxylic Acids ◽  
Spectroscopic Methods ◽  
Statistical Distributions ◽  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis ◽  
Axially Chiral ◽  
Aromatic Dicarboxylic Acids ◽  
The One ◽  
Cyclic Adducts

The “one-pot” synthesis of several homochiral macrocycles has been achieved by using π-electron-rich, electron-deficient or extended aromatic dicarboxylic acids in combination with an axially-chiral dibenzylic alcohol, derived from enantiomerically-pure BINOL. Two series of cyclic adducts with average molecular D 2 and D 3 molecular symmetries, respectively, have been isolated in pure forms. Their yields and selectivities deviate substantially from statistical distributions. NMR and CD spectroscopic methods are efficient and functional in order to highlight the variability of shapes of the covalent macrocyclic frameworks. The larger D 3 cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log K a = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation.

ChemInform Abstract: One-Pot Synthesis of Enantiomerically Pure (Methylenecyclopropyl) carbinol: A Key Intermediate to the Synthesis of the Causative Agent of Jamaican Vomiting Sickness.

ChemInform ◽  
2010 ◽  
Vol 25 (11) ◽  
pp. no-no
Author(s):  
K. OKUMA ◽  
Y. TANAKA ◽  
K. YOSHIHARA ◽  
A. EZAKI ◽  
G. KODA ◽  
...  
Keyword(s):  
Causative Agent ◽  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis

Efficient One-Pot Synthesis of Enantiomerically Pure 2-(Hydroxymethyl)morpholines

2007 ◽  
Vol 2007 (13) ◽  
pp. 2100-2106 ◽  
Author(s):  
Matthias Breuning ◽  
Malte Winnacker ◽  
Melanie Steiner
Keyword(s):  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis

Horseradish peroxidase — a biocatalyst for the one-pot synthesis of enantiomerically pure hydroperoxides and alcohols

1997 ◽  
Vol 117 (1-3) ◽  
pp. 321-328 ◽  
Author(s):  
Ute Hoch ◽  
Waldemar Adam ◽  
Rainer Fell ◽  
Chantu R. Saha-Möller ◽  
Peter Schreier
Keyword(s):  
Horseradish Peroxidase ◽  
One Pot ◽  
Enantiomerically Pure ◽  
One Pot Synthesis ◽  
The One
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