title: Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine.
abstract: A simple axially chiral amine catalyst promoted the regio-, diastereo-, and enantioselective conjugate addition of aldehydes to β-tosyl enones, which serve as ynone surrogates. The adducts were readily converted by treatment with L-selectride into less accessible enones with a γ stereogenic center. Such compounds cannot be prepared through the amine-catalyzed conjugate addition of aldehydes to ynones. The obtained enones underwent further conjugate addition of diorganozinc compounds in the presence of a copper catalyst.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan).
authors.forename: Taichi
authors.initials: T
authors.lastname: Kano
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan).
authors.forename: Hisashi
authors.initials: H
authors.lastname: Sugimoto
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan).
authors.forename: Hiroki
authors.initials: H
authors.lastname: Maruyama
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan). maruoka@kuchem.kyoto-u.ac.jp.
authors.forename: Keiji
authors.initials: K
authors.lastname: Maruoka
keywords: Michael addition; aldehydes; asymmetric catalysis; olefination; organocatalysis