The Journal of organic chemistry

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

R Vahabi, W Frey, J Pietruszka

Index: Vahabi, Roza; Frey, Wolfgang; Pietruszka, Joerg Journal of Organic Chemistry, 2013 , vol. 78, # 22 p. 11549 - 11559

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Citation Number: 7

Abstract

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.