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Abstract
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.
Original language | English |
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Pages (from-to) | 3001-3009 |
Number of pages | 9 |
Journal | Advanced Synthesis & Catalysis |
Volume | 351 |
Issue number | 17 |
DOIs | |
Publication status | Published - Nov 2009 |
Keywords
- asymmetric catalysis
- enantioselectivity
- esters
- ketenes
- N-heterocyclic carbenes
- organocatalysis
- INTERMOLECULAR STETTER REACTION
- DIELS-ALDER REACTIONS
- METHYL ALPHA-PHENYLPROPIONATE
- RING-OPENING POLYMERIZATION
- SYNTHESEN MIT KETENEN
- LOW CATALYST LOADINGS
- C-CARBOXYL TRANSFER
- ASYMMETRIC-SYNTHESIS
- ALPHA,BETA-UNSATURATED ALDEHYDES
- LIVING POLYMERIZATION
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- 1 Finished
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N-Heterocyclic Carbenes as Asymmetric: N-Heterocyclic Carbenes as Asymmetric Organocatalysts: Reaction Development
Smith, A. D. (PI)
1/04/07 → 30/09/10
Project: Standard