Abstract
A highly efficient Doyle–Kirmse reaction between alpha-arylidene diazosuccinimides and allyl thioethers in the presence of a cheaply and easily available copper catalyst for the concise and effective preparation of multifunctional 3-allyl-3-(thio) succinimides and 3-allenyl-3-(thio) succinimides in excellent yields (up to 90%) under mild conditions within a few hours has been developed. The target multifunctional succinimides may boast potential biological activities for the succinimide scaffold, and may be also used as potential new organic synthon for the preparations of new chemical and pharmaceutical entities or sulfoxide-olefin ligands. Afurther successful scale-uppreparationhas demonstrated the feasibility of the Doyle–Kirmse rearrangement and our new protocol.
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