title: Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.
abstract: Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, >10 g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5 mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98:2 enantiomeric ratio (er) in 5 h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Mandai
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Fujii
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Yasuhara
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Kenko
authors.initials: K
authors.lastname: Abe
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Mitsudo
authors.affiliation: Faculty of Engineering, Department of Chemistry and Bioengineering, Iwate University, Morioka, Iwate 020-8551, Japan.
authors.forename: Toshinobu
authors.initials: T
authors.lastname: Korenaga
authors.affiliation: Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.|Research Center of New Functional Materials for Energy Production, Storage and Transport Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.|Japan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
authors.forename: Seiji
authors.initials: S
authors.lastname: Suga