title: Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions.
abstract: Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Stefan
authors.initials: S
authors.lastname: Haubenreisser
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Thorsten H
authors.initials: TH
authors.lastname: Wöste
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Claudio
authors.initials: C
authors.lastname: Martínez
authors.affiliation: Graduate School of Engineering, Nagoya University, B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603 (Japan).
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona (Spain). kmuniz@iciq.es.|Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona (Spain). kmuniz@iciq.es.
authors.forename: Kilian
authors.initials: K
authors.lastname: Muñiz
keywords: alkenes; chirality; diacetoxylation; hydrogen bonding; hypervalent iodine