ALKYLATING AGENT AND 1,4-ADDITION PROCESS OF AN ALKYL GROUP ONTO AN ALPHA, BETA-UNSATURATED KETONE COMPOUND

摘要

This invention describes an alkylating agent that containsan aluminum reagent Alk3-m AlLm, in which Alk means a methyl,ethyl, n- or i-propyl, n-, i- or tert-butyl, pentyl, hexyl,heptyl or octyl group, which all can also be branched, L means anethoxy group, a chlorine or bromine atom, and m is equal to 1 or2, as an alkyl source or else zinc dimethyl as a methyl source,which contains in addition catalytic amounts of one or morecopper(I) and/or copper(II) compounds and one (or more) silylreagent(s) of general formula IIIR1R2R3SiZ (III),in whichR1, R2 and R3 can be the same or different and mean astraight-chain or branched-chain alkyl radical with 1 carbonatom, or in the branched-chain case, with 3 to 10 carbon atoms,an alkyl radical optionally substituted with 1 to 3 chlorineatoms or 1 to 3 straight-chain or branched-chain alkoxy or alkylradicals with 1 carbon atom or, in the branched-chain case, 3 to6 carbon atoms, andZ means a chlorine, bromine or iodine atom, the cyanoradical, a perfluoroalkylsulfonyloxy radical [(CnF2n+1SO2O-), withn = 1, 2, 3 or 4], the mesylate radical CH3SO2O-, the tosylradical p-CH3-C6H4-SO2O- or another leaving group,as well as a process for 1,4-addition of an alkyl group to an.alpha.,.beta.-unsaturated ketone or an .alpha.,.beta.-double unsaturated ketone or toan .alpha.,.beta.-unsaturated aldehyde with use of the agent according tothe invention. The alkylating agent yields biologically activecompounds in excellent yields and the new alkylating agent/process is distinguished by its environmental compatibilitybased on a CKW (chlorinated hydrocarbon)-free reaction medium.