title: Self-replication and amplification of enantiomeric excess of chiral multifunctionalized large molecules by asymmetric autocatalysis.
abstract: Self-replication of large chiral molecular architectures is one of the great challenges and interests in synthetic, systems, and prebiotic chemistry. Described herein is a new chemical system in which large chiral multifunctionalized molecules possess asymmetric autocatalytic self-replicating and self-improving abilities, that is, improvement of their enantioenrichment in addition to the diastereomeric ratio. The large chiral multifunctionalized molecules catalyze the production of themselves with the same structure, including the chirality of newly formed asymmetric carbon atoms, in the reaction of the corresponding achiral aldehydes and reagent. The chirality of the large multifunctionalized molecules controlled the enantioselectivity of the reaction in a highly selective manner to construct multiple asymmetric stereogenic centers in a single reaction.
authors.affiliation: Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html; Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science (Japan); Present address: Department of Materials Science and Engineering, University of Fukui, Bunkyo, Fukui, 910-8507 (Japan).
authors.forename: Tsuneomi
authors.initials: T
authors.lastname: Kawasaki
authors.forename: Mai
authors.initials: M
authors.lastname: Nakaoda
authors.forename: Yutaro
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kanto
authors.forename: Nanako
authors.initials: N
authors.lastname: Kuruhara
authors.forename: Kenji
authors.initials: K
authors.lastname: Hosoi
authors.forename: Itaru
authors.initials: I
authors.lastname: Sato
authors.forename: Arimasa
authors.initials: A
authors.lastname: Matsumoto
authors.forename: Kenso
authors.initials: K
authors.lastname: Soai
keywords: asymmetric amplification; asymmetric catalysis; autocatalysis; chirality; enantioselectivity