An efficient synthesis of C2-symmetric chiral binaphthyl ketone catalysts.
An efficient synthesis of C2-symmetric chiral binaphthyl ketones 1a and b, effective catalysts for asymmetric epoxidation, is reported. The key features of this synthesis are Co(salen)-catalyzed macrolactonization of racemic 1,1'-binaphthyl-2,2'-dicarboxylic acid monoglycidyl esters 3a and b and lipase-catalyzed enantioselective acylation of resulting 11-membered cyclic binaphthyl alcohols 4a and b.
Furutani
T
T
Product & Technology Development Laboratory, Tanabe Seiyaku Co. Ltd., Osaka, Japan.
Hatsuda
M
M
Shimizu
T
T
Seki
M
M
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D004852:Epoxy Compounds; D007659:Ketones; D007783:Lactones; D009281:Naphthalenes; D008049:Lipase