Journal
ORGANIC LETTERS
Volume 11, Issue 1, Pages 105-108Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802448c
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Funding
- NIH [GM73072]
- GlaxoSmithKline
- AstraZeneca
- Boerhinger-Ingelheim
- Wacker Chemical Corp.
- FMCLithium
- Sloan Foundation
- Integrated Molecular Structure Education and Research Center (IMSERC)
- NSF [CHE-9871268]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM073072] Funding Source: NIH RePORTER
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N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4 through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst Is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.
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