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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.

DOI: 10.1021/ja910750b (free Supporting Information)


Abstract

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.

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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.


Key Words

Allylic Alcohols, 1,3-Dienes


ID: J48-Y2010-0740