title: (1,2-Diaminoethane-1,2-diyl)bis(N-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts.
abstract: A new efficient and highly recyclable organocatalyst has been developed for asymmetric cross-aldol reactions under neat conditions in ketone-ketone, ketone-aldehyde, and aldehyde-aldehyde systems. The catalyst features two prolinamide fragments and a C2-symmetrical (1,2-diaminoethane-1,2-diyl)bis(N-methylpyridinium) group. The catalyst retained high activity and excellent stereoselection over the operating period of more than 830 h (25 cycles). An ab initio theoretical investigation explained the absolute configuration of the products and different stereoinduction levels for designed diastereomeric organocatalysts.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky Prospect, 119991 Moscow, Russia.|Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology , 9 Miusskaya Square, 125047 Moscow, Russia.
authors.forename: Vladislav G
authors.initials: VG
authors.lastname: Lisnyak
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky Prospect, 119991 Moscow, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Kucherenko
authors.affiliation: Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
authors.forename: Edward F
authors.initials: EF
authors.lastname: Valeev
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , 47 Leninsky Prospect, 119991 Moscow, Russia.
authors.forename: Sergei G
authors.initials: SG
authors.lastname: Zlotin