title: Vinylogy in nitronates: utilization of α-aryl conjugated nitroolefins as a nucleophile for a highly stereoselective aza-Henry reaction.
abstract: The vinylogous reactivity of α,β-disubstituted nitroolefins was uncovered through the facile generation of the corresponding α-substituted vinylogous nitronates and their use in the development of a highly diastereo- and enantioselective aza-Henry reaction with N-Boc aldimines under the catalysis of chiral ammonium betaines. The novel vinylogous nitronates undergo stereoselective bond formation at the sterically encumbered α-position exclusively, allowing the construction of contiguous tertiary-quaternary stereogenic carbon centers.
authors: Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan. tooi@apchem.nagoya-u.ac.jp.
authors: Keigo
authors: K
authors: Oyaizu
authors: Daisuke
authors: D
authors: Uraguchi
authors: Takashi
authors: T
authors: Ooi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001622:Betaine / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007097:Imines; D009574:Nitro Compounds; D014753:Vinyl Compounds; D001622:Betaine