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Studies Towards New Reagents for Asymmetric Hydroboration: Synthesis of Racemic Trans-2,5-diisopropylborolane
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1  Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland

Abstract: The cyclic hydroboration of 2,7-dimethyl-2,6-octadiene was studied. It was found that the stereochemical outcome of the reaction was dependent upon the solvent, temperature, time, and the nature of the borane reagent. Monobromoborane in carbon tetrachloride at 76 oC gave after 8 hr a 4:1 mixture of trans:cis-2,5-diisopropylborolane. Pure racemic trans-2,5-diisopropyl borolane was isolated following selective complexation of the cis-2,5-diisopropylborolane with 1-(2-hydroxyethyl)-pyrrolidine.
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