Asymmetric aldol reaction using boron enolates

Abstract

The protocol for the preparation of boron enolates and their subsequent reaction with aldehydes is described, providing convenient access to ߭hydroxy ketones in good yields and with high stereoselectivities. The reaction consists of three steps; firstly the ketone is rapidly converted to the corresponding boron enolate, by exposure to a chlorodialkylborane and tertiary amine base, which is then reacted in situ with the aldehyde. Finally, oxidative workup of the resultant boron aldolate provides aldol adduct. The reaction procedure requires approximately 28 h to complete over a two day period, consisting of 5 h to set up the reaction, whereupon the reaction mixture is left at -20 àovernight (16 h), followed by 7 h for workup and purification.