Journal
ORGANIC LETTERS
Volume 14, Issue 16, Pages 4206-4209Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301879a
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [23710245] Funding Source: KAKEN
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A novel three-component coupling between trimethylsilylmethylphosphonate, acyl fluoride, and aldehyde has been developed. A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to the acyl fluoride and Horner-Wadsworth-Emmons reaction of an aldehyde with the lithio-beta-ketophosphonate generated in situ by desilylation at the alpha-position of the alpha-silyl-beta-ketophosphonate by fluoride took place cleanly in a one-pot operation. Various E- and Z-enones were obtained in high yields with high stereoselectivities by this one-pot procedure.
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