Synthesis of diboranes
Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts via the intermediacy of 1,2-bonded diboronates.
L. Fang, L. Yan, F. Haeffner, J. P. Morken, J. Am. Chem. Soc., 2016, 138, 2508-2511.
A Pt-catalyzed enantioselective addition of bis(pinacolato)diboron to various terminal alkenes occurs in the presence of a readily available chiral phosphonite ligand. While oxidation of the intermediate 1,2-bis(boronate) ester provides a chiral 1,2-diol as the reaction product, homologation/oxidation furnishes a chiral 1,4-diol.
L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 13210-13211.
A rhodium-catalyzed enantioselective syn addition of bis(catecholato)diboron to simple alkenes in the presence of (S)-Quinap provides enantioenriched 1,2-diols after subsequent oxidation. The substrate scope, the reaction mechanism, and competing pathways are discussed.
S. Trudeau, J. M. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem., 2005, 70, 9538-9544.