Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines.
A mild ring opening of vinyl epoxides and aziridines with B(2)Pin(2) catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bishomoallylic alicyclic 1,3-diols and 1,3-amino alcohols with remarkably high stereoselectivities. Valuable trans-bisallylic 1,4-amino alcohols can be obtained by a simple oxidation.
Crotti
Stefano
S
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Bertolini
Ferruccio
F
Macchia
Franco
F
Pineschi
Mauro
M
D001388:Aziridines / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D001388:Aziridines; D001896:Boron Compounds; D004852:Epoxy Compounds; D014753:Vinyl Compounds; D009532:Nickel