title: Highly Z- and enantioselective ring-opening/cross-metathesis reactions catalyzed by stereogenic-at-Mo adamantylimido complexes.
abstract: The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50-85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (>or=87:13 Z/E).
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Ismail
authors.initials: I
authors.lastname: Ibrahem
authors.forename: Miao
authors.initials: M
authors.lastname: Yu
authors.forename: Richard R
authors.initials: RR
authors.lastname: Schrock
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D000475:Alkenes; D002384:Catalysis; D003500:Cyclization; D008982:Molybdenum; D009942:Organometallic Compounds; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D009942:Organometallic Compounds; D011714:Pyrans; D008982:Molybdenum