title: α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocyclobutenones with Tetrasubstituted Carbon.
abstract: A method for asymmetric α-arylation of α-amino acid derivatives via memory of chirality has been developed. Addition of axially chiral enolates, generated from α-amino acid derivatives, to in situ generated arynes, followed by intramolecular C-acylation of the resulting aryl metallic species, gave benzocyclobutenones with a tetrasubstituted carbon with retention of configuration in up to 99% ee.
authors.affiliation: Institute for Chemical Research, Kyoto University , Uji 611-0011, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Kasamatsu
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Yoshimura
authors.affiliation: Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors.forename: Attila
authors.initials: A
authors.lastname: Mandi
authors.affiliation: Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors.forename: Tohru
authors.identifier: 0000-0002-4965-7383
authors.initials: T
authors.lastname: Taniguchi
authors.affiliation: Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors.forename: Kenji
authors.identifier: 0000-0002-1424-1054
authors.initials: K
authors.lastname: Monde
authors.affiliation: Institute for Chemical Research, Kyoto University , Uji 611-0011, Japan.
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.affiliation: Institute for Chemical Research, Kyoto University , Uji 611-0011, Japan.
authors.forename: Takeo
authors.identifier: 0000-0002-9959-0420
authors.initials: T
authors.lastname: Kawabata