Regio- and Stereoselective Ni-Catalyzed 1,4-Hydroboration of 1,3-Dienes: Access to Stereodefined (Z)-Allylboron Reagents and Derived Allylic Alcohols
Robert J. Ely and James P. Morken*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: morkenbc.edu
R. J. Ely, J. P. Morken, J. Am. Chem. Soc., 2010, 132, 2534-2535.
A catalytic regio- and stereoselective 1,4-hydroboration with pinacolborane in the presence of Ni(cod)2 and PCy3 exhibits broad substrate scope operating on a range of substituted 1,3-dienes and occurs with generally high levels of selectivity and efficiency. The intermediate allylboronate can be oxidized to stereodefined allylic alcohols or can be used in stereoselective carbonyl addition reactions.
see article for more examples
Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration
H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 9134-9135.
Ni(0)-Catalyzed 1,4-Selective Diboration of Conjugated Dienes
R. J. Ely, J. P. Morken, Org. Lett., 2010, 12, 4348-4351.