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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

Overview
Journal J Am Chem Soc
Publisher American Chemical Society
Specialty Chemistry
Date 2010 Feb 9
PMID 20136142
Citations 25
Authors
Robert J Ely
James P Morken
Affiliations
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Abstract

A catalytic regio- and stereoselective 1,4-hydroboration of 1,3-dienes was accomplished with pinacolborane in the presence of Ni(cod)(2) and PCy(3). This reaction exhibits broad substrate scope operating on a range of substituted dienes and occurs with generally high levels of selectivity and efficiency. Reactivity patterns suggest that the reactive conformation of the diene is the S-cis form. The intermediate allylboronate can be oxidized to stereodefined allylic alcohols or can be used in stereoselective carbonyl addition reactions.

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References
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