"Bisguanidinium-catalyzed remote enantioselective desymmetrization with" by Wenchao Chen, Li Chen et al.
In this work, we described a remote desymmetrization reaction in which cesium carboxylate, in the presence of bisguanidinium as catalyst, was added to (cis)-α,α′-dibromocyclohexanone to access 6-oxocyclohex-1-enyl ester via a 1,2-acyl shift in a highly enantioselective fashion. In this process, the carboxylate initiated a nucleophilic attack, and then a keto-enol tautomerism led to a 1,2-acyl shift to the neighboring alcohol. Key intermediates were isolated and determined using single-crystal X-ray crystallography. The remote desymmetrization that includes stepwise SN2 and intramolecular a...
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