title: Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents.
abstract: The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr*Me2S. The substitution proceeds with anti SN2' pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.
authors.affiliation: Department of Biomolecular Engineering, Tokyo Institute of Technology, Yokohama, Japan.
authors.forename: Yohei
authors.initials: Y
authors.lastname: Kiyotsuka
authors.forename: Hukum P
authors.initials: HP
authors.lastname: Acharya
authors.forename: Yuji
authors.initials: Y
authors.lastname: Katayama
authors.forename: Tomonori
authors.initials: T
authors.lastname: Hyodo
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Kobayashi
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010848:Picolinic Acids / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000838:Anions; D007202:Indicators and Reagents; D010848:Picolinic Acids; D010880:Piperidines; C030614:picolinic acid; C084823:pipradrol