title: Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents.
abstract: Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.
authors.affiliation: Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ (United Kingdom).
authors.forename: Emma
authors.initials: E
authors.lastname: Packard
authors.forename: David D
authors.initials: DD
authors.lastname: Pascoe
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
authors.forename: Théo P
authors.initials: TP
authors.lastname: Gonçalves
authors.forename: David C
authors.initials: DC
authors.lastname: Harrowven
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002070:Butadienes / Q000737:chemistry*; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry*; D045782:Hemiterpenes / Q000737:chemistry*; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry*; D015018:Ytterbium / Q000737:chemistry*
chemical_list: D001688:Biological Products; D002070:Butadienes; D003503:Cyclobutanes; D045782:Hemiterpenes; D006873:Hydroquinones; D007659:Ketones; D009942:Organometallic Compounds; D010420:Pentanes; C005059:isoprene; D015018:Ytterbium
keywords: density functional calculations; flow chemistry; natural products; rearrangement; ytterbium