jo402130u_si_004.cif (25.99 kB)
Synthesis of Highly-Substituted Enantiomerically Pure Allylboronic Esters and Investigation of Their Stereoselective Addition to Aldehydes
dataset
posted on 2013-11-15, 00:00 authored by Roza Vahabi, Wolfgang Frey, Jörg PietruszkaDiastereomerically
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.