N‐Heterocyclic Carbene‐Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes | Zendy

Concellón Carmen | Zendy; Duguet Nicolas | Zendy; Smith Andrew D. | Zendy

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N‐Heterocyclic Carbene‐Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Author(s) -

Concellón Carmen,

Duguet Nicolas,

Smith Andrew D.

Publication year - 2009

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200900538

Subject(s) - chemistry , enantioselective synthesis , carbene , alkyl , phenols , catalysis , organic chemistry , combinatorial chemistry , stereochemistry

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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