Synthesis of Highly-Substituted Enantiomerically Pure Allylboronic Esters and Investigation of Their Stereoselective Addition to Aldehydes
2013-11-15T00:00:00Z (GMT) by
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 <i>E</i> configuration; their synthesis and the mechanism of the reaction is proposed here.
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