O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate.
The approach using pyrrolidine enamine as substrate has been studied for this synthesis, and an important catalyst structural feature has been developed. After survey of pyrrolidine-based Brønsted acid catalyst, tetrazole catalyst (3f) was found to be optimal in synthesis of aminooxy carbonyl compounds in high yields, with complete enantioselectivity not only for aldehydes but also for ketones.
Momiyama
Norie
N
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
Torii
Hiromi
H
Saito
Susumu
S
Yamamoto
Hisashi
H
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D007659:Ketones; D009603:Nitroso Compounds; D011759:Pyrrolidines; D013777:Tetrazoles; C045574:1H-tetrazole