Novel asymmetric synthesis of optically active .delta.- and .gamma.-lactones using a C2-chiral auxiliary

1987 ◽  
Vol 109 (23) ◽  
pp. 7188-7189 ◽  
Author(s):  
Akio Sakamoto ◽  
Yukio Yamamoto ◽  
Junichi Oda
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Chiral Auxiliary

scholarly journals Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

2018 ◽  
Vol 14 ◽  
pp. 593-602 ◽  
Author(s):  
Romain Sallio ◽  
Stéphane Lebrun ◽  
Frédéric Capet ◽  
Francine Agbossou-Niedercorn ◽  
Christophe Michon ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Phase Transfer ◽  
Benzodiazepine Receptor ◽  
Optically Active ◽  
Chiral Auxiliary ◽  
Phase Transfer Catalyst ◽  
Receptor Agonists ◽  
Michael Acceptor

A new asymmetric organocatalyzed intramolecular aza-Michael reaction by means of both a chiral auxiliary and a catalyst for stereocontrol is reported for the synthesis of optically active isoindolinones. A selected cinchoninium salt was used as phase-transfer catalyst in combination with a chiral nucleophile, a Michael acceptor and a base to provide 3-substituted isoindolinones in good yields and diastereomeric excesses. This methodology was applied to the asymmetric synthesis of a new pazinaclone analogue which is of interest in the field of benzodiazepine-receptor agonists.

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.

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