Allylboronic acids are synthetically very useful building blocks for chemical transformations. Due to their instability under ambient condition, the synthetic utility of allylboronic acids is not known broadly. Recently we reported that allylboronic acids react with a range of carbonyl compounds without any additives.1,2 As part of our studies, now we have demonstrated that, allylboronic acids react with imines and indoles under very mild conditions in absence of additive. The reactions proceed under mild conditions to afford high regio- and stereoselective homoallylic amines (Scheme 1). Experimental and theoretical studies showed, E-imine isomerize to Z-imine prior to allylation and this isomerization facilitated by the allylboroxine that formed in the dry reaction conditions.3 Scheme 1. Allylboration of imine by allylboronic acids.References:(1) Raducan, M.; Alam, R.; Szab�, K. J. Angew. Chem. Int. Ed. 2012  , 51, 13050.(2) Alam, R.; Raducan, M.; Eriksson, L.; Szab�, K. J. Org. Lett. 2013  , 15, 2546.(3) Alam, R.; Das, A.; Huang, G.; Eriksson, L.; Himo, F.; Szabo, K. J. Chem. Sci. 2014  . DOI 10.1039/C4SC00415A

Highly diastereoselective allylboration of imines and indoles: In situ isomerization of imines by allylboroxines

248th National Meeting (2014)

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