title: Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.
abstract: Multicomponent catalytic enantioselective transformations that entail the combination of butadiene or isoprene (common feedstock), an enoate (prepared in one step) and B2 (pin)2 (commercially available) are presented. These processes constitute an uncommon instance of conjugate addition of an allyl moiety and afford the desired products in up to 83 % yield and 98:2 enantiomeric ratio. Based on DFT calculations stereochemical models and rationale for the observed profiles in selectivity are provided.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Xiben
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Fanke
authors.initials: F
authors.lastname: Meng
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Torker
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Ying
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA. amir.hoveyda@bc.edu.
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D045782:Hemiterpenes / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010420:Pentanes / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D001896:Boron Compounds; D002070:Butadienes; D045782:Hemiterpenes; D009942:Organometallic Compounds; D010420:Pentanes; C005059:isoprene; D003300:Copper
keywords: boron; conjugate additions; copper; enantioselective catalysis; synthetic methods