title: O-nitroso aldol synthesis: Catalytic enantioselective route to alpha-aminooxy carbonyl compounds via enamine intermediate.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
authors.forename: Norie
authors.initials: N
authors.lastname: Momiyama
authors.forename: Hiromi
authors.initials: H
authors.lastname: Torii
authors.forename: Susumu
authors.initials: S
authors.lastname: Saito
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: 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
chemical_list: D000447:Aldehydes; D000588:Amines; D007659:Ketones; D009603:Nitroso Compounds; D011759:Pyrrolidines; D013777:Tetrazoles; C045574:1H-tetrazole