Chiral N‐heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2‐phenylphenol to unsymmetrical alkylarylketenes, delivering α‐alkyl‐α‐arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee ). Enantiodivergent stereochemical outcomes are observed using 2‐phenylphenol and benzhydrol in the NHC‐promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.
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Concellón et al. (2009) studied this question.
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