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Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes

Hee Yeon Cho and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: morkenbc.edu

H. Y. Cho, J. P. Morken, J. Am. Chem. Soc., 2008, 130, 16140-16141.

DOI: 10.1021/ja806113v (free Supporting Information)


Abstract

A regio- and diastereoselective nickel-catalyzed reductive coupling of carbonyls with dienes in the presence of a stoichiometric amount of bis(pinacolato)diboron furnishes allyl boronic esters as the reaction product, which was readily converted to the derived allylic alcohol by oxidative workup.

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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.


Key Words

Homoallylic Alcohols, Hydroxylation


ID: J48-Y2008-3600