Isomer-directed process for producing asymmetric ketones using catalytic claisen rearrangement of allylic ethers, intermediates, and uses of products and intermediates of process in perfumery

摘要

Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: <IMAGE> wherein one of Z1 or Z2 is the moiety: <IMAGE> and the other of Z1 or Z2 is hydrogen; wherein R11 and R21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R11 and R21 are not both hydrogen or wherein R11 and R21 taken together: (i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or (ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene; and wherein R6, R7 and R8 are the same or different and each represents hydrogen or methyl, using a catalytic Claisen rearrangement of allylic ethers previously formed by reacting substituted or unsubstituted allylic alcohols defined according to the structure: <IMAGE> with dialkyl ketals defined according to the structure: <IMAGE> wherein R4 and R5 represent the same or different C1-C4 alkyl. Also described are compounds and processes for using same in perfumery defined according the structures: <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> +TR <IMAGE> Also described are certain diallylic ethers defined according to the generic structure: <IMAGE>