Synthesis of (2S,2′S)-bimorpholine N,N′-quaternary salts as chiral phase transfer catalysts

2007 ◽  
Vol 18 (1) ◽  
pp. 137-141 ◽  
Author(s):  
Kristin Lippur ◽  
Tõnis Kanger ◽  
Kadri Kriis ◽  
Tiiu Kailas ◽  
Aleksander-Mati Müürisepp ◽  
...  
Keyword(s):  
Phase Transfer ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Quaternary Salts ◽  
Chiral Phase Transfer Catalysts

scholarly journals Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts

2011 ◽  
Vol 8 (3) ◽  
pp. 1293-1297
Author(s):  
Lalit Sharma ◽  
Subhash Chander Sharma ◽  
Saroj
Keyword(s):  
Nonionic Surfactants ◽  
Phase Transfer ◽  
Enantiomeric Excess ◽  
Hydrocarbon Chain ◽  
Asymmetric Epoxidation ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Quaternary Salts ◽  
Chiral Phase Transfer Catalysts ◽  
Branched Chain

Quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose were explored as chiral phase transfer catalysts for the asymmetric epoxidation of chalcone. Quaternary salts used in the present study, were void of any branched chain or long hydrocarbon chain, whereas the sugar based nonionic surfactants have a long hexadecyl moiety as tail. It was observed that quaternary salts showed no activity as phase transfer catalysts but sugar based nonionic surfactants acted as chiral phase transfer catalysts. It was also revealed that hydrophilicity of the surfactant favors more yield whereas stereochemistry governs enantioselectivity. (6,6'-Hexadecylimino) bis(6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose) was found to be the most suitable chiral phase transfer catalyst, resulting asymmetric epoxidation of chalcone with 90% yield and 16.5% enantiomeric excess (ee).

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