Asymmetric synthesis of tetrahydrofurans by diastereoselective [3+2] cycloaddition of allylsilanes with α-keto esters bearing an optically active cyclitol as a chiral auxiliary

1994 ◽  
Vol 35 (45) ◽  
pp. 8401-8404 ◽  
Author(s):  
Takahiko Akiyama ◽  
Takuya Yasusa ◽  
Keiichiro Ishikawa ◽  
Shoichiro Ozaki
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Chiral Auxiliary ◽  
Keto 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.

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