title: Copper-catalyzed asymmetric three-component borylstannation: enantioselective formation of C-Sn bond.
abstract: In summary, a first copper-catalyzed synthesis of α-aryl-β-borylstannane compounds was accomplished through three-component borylstannation of aryl-substituted alkenes. In the exploration of an asymmetric variant, chiral sulfinylphosphine ligands proved advantageous in controlling stereochemistry of B-Cu addition and in promoting transmetalation of enantioenriched alkyl-Cu species. The stereochemical outcome supported a sequential syn-borylcupration and configuration-retentive transmetalation mechanism. Moreover, α-chiral β-borylstannanes were easily transformed into a diverse array of secondary alkylstannanes and triarylethane with high enantiomeric purity. The applications of chiral sulfinylphosphine ligands to other tandem Cu-B addition reactions are currently under investigation in our group.
authors: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China).
authors: Tao
authors: T
authors: Jia
authors: Peng
authors: P
authors: Cao
authors: Ding
authors: D
authors: Wang
authors: Yazhou
authors: Y
authors: Lou
authors: Jian
authors: J
authors: Liao
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
chemical_list: D001896:Boron Compounds; D009942:Organometallic Compounds; D014001:Tin; D002244:Carbon; D003300:Copper
keywords: asymmetric synthesis; borylation; copper; homogeneous catalysis; stannation