A highly enantioselective and diastereoselective synthesis of cyclobutanes via boronic esters |
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Authors: | Man H W Hiscox W C Matteson D S |
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Institution: | Department of Chemistry, Washington State University, Pullman 99164-4630, USA. |
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Abstract: | formula: see text] Deprotonation of enantiopure (R,R)-1,2-dicyclohexyl-1,2-ethanediol 1-chloro-4-cyanobutylboronates 5 with LDA followed by treatment with anhydrous magnesium bromide yields (R)-(trans-2-cyanocyclobutyl)boronic esters 7 in high diastereomeric and enantiomeric purity. No cyclobutane formation has been observed in the absence of at least a catalytic amount of magnesium halide. |
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