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Synthesis of Highly-Substituted Enantiomerically Pure Allylboronic Esters and Investigation of Their Stereoselective Addition to Aldehydes

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posted on 2013-11-15, 00:00 authored by Roza Vahabi, Wolfgang Frey, Jörg Pietruszka
Diastereomerically pure allylboronates bearing the readily available tartrate derivative were obtained via sigmatropic rearrangement. Allyl additions were performed, and the influence of γ-disubstituted allylboronates was studied. Highly γ-substituted boronic esters were found to lead to the corresponding enantiomerically enriched homoallyl alcohols with exclusively E configuration; their synthesis and the mechanism of the reaction is proposed here.