Synthesis of 3-hydroxy-1-alkenylboronates via phosphine stabilized borylzirconacyclopropenes.
Zirconacyclopropenylboronates can be stabilized to dimerization by complexation with tributylphosphine; the phosphine stabilized zirconacycle boronates react with aliphatic and aromatic ketones and aldehydes at C2 of the triple bond to give the previously unknown 3-hydroxyvinylboronates in 61-80% isolated yields.
Al Quntar
Abed Al Aziz
AA
Department of Medicinal Chemistry and Natural Products, Hebrew University, Jerusalem, 91120, Israel.
Botvinik
Alina
A
Rubinstein
Abraham
A
Srebnik
Morris
M
D000447:Aldehydes / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D015040:Zirconium / Q000737:chemistry*
D000447:Aldehydes; D001897:Boronic Acids; D003521:Cyclopropanes; D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D010720:Phosphines; C021985:cyclopropene; D015040:Zirconium; C044646:phosphine