title: Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination sequence.
abstract: A two-step sequence for the asymmetric formal α-allylation of nitroalkanes is disclosed. This new methodology relies on the development of a highly diastereo- and enantioselective conjugate addition of nitroalkanes to vinylic 2-phenyl-1H-tetrazol-5-ylsulfones using chiral triaminoiminophosphorane as a requisite base catalyst and subsequent Julia-Kocienski olefination under kinetic conditions.
authors.affiliation: 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.forename: Daisuke
authors.initials: D
authors.lastname: Uraguchi
authors.forename: Shinji
authors.initials: S
authors.lastname: Nakamura
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Sasaki
authors.forename: Yuki
authors.initials: Y
authors.lastname: Konakade
authors.forename: Takashi
authors.initials: T
authors.lastname: Ooi
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D010753:Phosphoranes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D007097:Imines; D010753:Phosphoranes