Asymmetric Synthesis of β-Amino Esters by Aza-Michael Reaction of α,β-Unsaturated Amides Using (S,S)-(+)-Pseudoephedrine as Chiral Auxiliary

2004 ◽  
Vol 69 (7) ◽  
pp. 2588-2590 ◽  
Author(s):  
Juan Etxebarria ◽  
Jose L. Vicario ◽  
Dolores Badia ◽  
Luisa Carrillo
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Chiral Auxiliary ◽  
Amino Esters

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.

scholarly journals Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary

1995 ◽  
Vol 60 (14) ◽  
pp. 4331-4338 ◽  
Author(s):  
Hendrik L. van Maanen ◽  
Henk Kleijn ◽  
Johann T. B. H. Jastrzebski ◽  
Jan Verweij ◽  
Antonius P. G. Kieboom ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Condensation Reaction ◽  
Chiral Auxiliary ◽  
Beta Lactams ◽  
Amino Esters ◽  
Ester Enolate

ChemInform Abstract: Asymmetric Synthesis of β-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using α-Amino Esters as the Chiral Auxiliary.

ChemInform ◽  
2010 ◽  
Vol 26 (48) ◽  
pp. no-no
Author(s):  
H. L. VAN MAANEN ◽  
H. KLEIJN ◽  
J. T. B. H. JASTRZEBSKI ◽  
J. VERWEIJ ◽  
A. P. G. KIEBOOM ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Condensation Reaction ◽  
Chiral Auxiliary ◽  
Amino Esters ◽  
Ester Enolate

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: Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines.

ChemInform ◽  
2014 ◽  
Vol 45 (3) ◽  
pp. no-no
Author(s):  
Santos Fustero ◽  
Lidia Herrera ◽  
Ruben Lazaro ◽  
Elsa Rodriguez ◽  
Miguel A. Maestro ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction

Asymmetric Synthesis of Iridoid Derivatives Using Resolved 2-Phenylindoline as a Chiral Auxiliary

2008 ◽  
Vol 2008 (35) ◽  
pp. 5915-5921 ◽  
Author(s):  
Ellen M. Santangelo ◽  
Ilme Liblikas ◽  
Anoma Mudalige ◽  
Karl W. Törnroos ◽  
Per-Ola Norrby ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary
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