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Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration

Heather E. Burks, Laura T. Kliman and James P. Morken*

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

H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 9134-9135.

DOI: 10.1021/ja809610h (free Supporting Information)



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Abstract

Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin)2) to conjugated dienes enables an asymmetric 1,4-dihydroxylation of 1,3-dienes. Dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway.

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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

R. J. Ely, J. P. Morken, J. Am. Chem. Soc., 2010, 132, 2534-2535.

Pt-Catalyzed Enantioselective Diboration of Terminal Alkenes with B2(pin)2

L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 13210-13211.

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

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


Key Words

Allylic Alcohols, Hydrogen Peroxide


ID: J48-Y2009-2040