Chemistry

Prof. Kalman Szabo
Department of Organic Chemistry, Stockholm University, Sweden

Recently we have developed an efficient palladium-catalyzed method for synthesis (and isolation) of functionalized allylboronic acids from allylic alcohols and (commercially available) diboronic acid.¹Allylboronic acids are usually more reactive than allylboronic ester (such as allyl-Bpin) reagents. We have found that these compounds are reacting with ketones,²imines³and hydrazones⁴under mild neutral conditions to give homoallylic alcohols and amines with remarkably high regio- and stereoselectivity. Allylboronic acids also react in cross-coupling reactions affording the branched allylic isomer.⁵Recent results on the asymmetric allylation of ketones affording homoallylic alcohols with adjacent quaternary stereocenters,⁶as well as new applications for selective cross-coupling reactions⁷will also be presented.

(1)  Raducan, M.; Alam, R.; Szabó, K. J. Angew. Chem. Int. Ed. 2012, 51, 13050.

(2)  Alam, R.; Raducan, M.; Eriksson, L.; Szabó, K. J. Org. Lett. 2013, 15, 2546.

(3)  Alam, R.; Das, A.; Huang, G.; Eriksson, L.; Himo, F.; Szabó, K. J. Chem. Sci. 2014, 5, 2732.

(4)  Das, A.; Alam, R.; Eriksson, L.; Szabó, K. J. Org. Lett. 2014, 16, 3808.

(5)  Sebelius, S.; Olsson, V. J.; Wallner, O. A.; Szabó, K. J. J. Am. Chem. Soc. 2006, 128, 8150.

(6)  Alam, R.; Vollgraff, T.; Eriksson, L.; Szabó, K. J. J. Am. Chem. Soc. 2015, 137, 11262−11265.

(7)  Das, A.; Wang, D.; Belhomme, M.-C.; Szabó, K. J. Org. Lett. 2015.