title: Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction.
abstract: An efficient organocascade quadruple reaction was conducted to synthesize a functionalized spiropolycyclic scaffold in high chemical yields (43-80%) and excellent levels of stereoselectivity (up to >19:1 dr and 99% ee). The quadruple reaction proceeded smoothly between 1,3-indanedione and aromatic aldehydes with concomitant desymmetrization of prochiral 4-substituted cyclohexanones through the Knoevenagel/Michael/aldol/aldol reaction sequence catalyzed by a bifunctional thiourea catalyst. Two of the formed products were transformed into spirocyclic epoxides containing four contiguous quaternary centers.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Yun-Pu
authors.initials: YP
authors.lastname: Chang
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Ramani
authors.initials: R
authors.lastname: Gurubrahamam
authors.affiliation: Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
authors.forename: Kwunmin
authors.initials: K
authors.lastname: Chen