title: Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.
abstract: The first Ir-catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities.
authors.affiliation: Departments of Chemistry, University of California, Berkeley, CA, 94720, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.affiliation: Departments of Chemistry, University of California, Berkeley, CA, 94720, USA. jhartwig@berkeley.edu.
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D010710:Phosphates; D012821:Silanes; D007495:Iridium
keywords: 1,1′-substituted olefins; allylic asymmetric substitution; allylic phosphates; dioxinones; iridium catalysis