Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination.
[reaction: see text] Highly enantioselective Reformatsky reaction of ketones was accomplished using cinchona alkaloids as chiral ligands. Chelation with the sp(2)-nitrogen adjacent to the reactive carbonyl center contributed the enantioface discrimination for the high enantioselectivities.
Medicinal Chemistry Research Laboratories, Takeda Chemical Industries, Ltd., Osaka 532-8686, Japan.
Akio
A
Ojida
Toru
T
Yamano
Naohiro
N
Taya
Akihiro
A
Tasaka
D000438:Alcohols / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002930:Cinchona Alkaloids / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000302:isolation & purification; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000302:isolation & purification; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D002930:Cinchona Alkaloids; D004952:Esters; D006880:Hydroxy Acids; D007659:Ketones; C010086:cinchonine