title: Enantioselective tandem O-nitroso Aldol/Michael reaction.
abstract: This communication presents studies that illustrated nitroso Diels-Alder adduct has been obtained in uniformly high enantioselectivity via a tandem nitroso aldol/Michael reaction using an amine catalyst. The regiochemical outcome of this construction is documented to be the opposite to that of the normal nitroso aldol reaction, which has been determined by X-ray analysis. The reaction of the enone with silver-BINAP catalyst has also been investigated in conjunction with the control of regiochemistry in a stepwise process.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Yuhei
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Norie
authors.initials: N
authors.lastname: Momiyama
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis; D009281:Naphthalenes / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; C406943:BINAP, 2-naphthol; D007659:Ketones; D009281:Naphthalenes; D009603:Nitroso Compounds; D012834:Silver; C012456:nitrosobenzene