Synthesis of beta,beta-disubstituted vinyl boronates via the ruthenium-catalyzed Alder ene reaction of borylated alkynes and alkenes.
Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding beta,beta-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the ene subunit across the alkyne, which is the opposite stereochemical outcome observed for other internal alkynes.
Hansen
Eric C
EC
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
Lee
Daesung
D
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D012428:Ruthenium / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000475:Alkenes; D000480:Alkynes; D001897:Boronic Acids; D014753:Vinyl Compounds; D012428:Ruthenium