A mild ring opening of vinyl- epoxides and aziridines with B2Pin2 catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bis-homoallylic alicyclic 1,3-diols and 1,3-aminoalcohols with remarkably high stereoselectivities. Valuable trans-bis-allylic 1,4-aminoalcohols can be obtained by a simple oxidation.
Nickel-Catalyzed Borylative Ring-Opening of Vinyl Epoxides and Aziridines
PINESCHI, MAURO
2009-01-01
Abstract
A mild ring opening of vinyl- epoxides and aziridines with B2Pin2 catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bis-homoallylic alicyclic 1,3-diols and 1,3-aminoalcohols with remarkably high stereoselectivities. Valuable trans-bis-allylic 1,4-aminoalcohols can be obtained by a simple oxidation.File in questo prodotto:
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