Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 17, Pages 3001-3009Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900538
Keywords
asymmetric catalysis; enantioselectivity; esters; ketenes; N-heterocyclic carbenes; organocatalysis
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Funding
- Royal Society
- Ministerio de Educacion y Ciencia (CC)
- Leverhulme Trust (ND)
- Engineering and Physical Sciences Research Council [EP/E03795X/1] Funding Source: researchfish
- EPSRC [EP/E03795X/1] Funding Source: UKRI
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Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-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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