期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 361, 期 3, 页码 502-509出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801035
关键词
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资金
- National Science Foundation [CHE-1464744]
- MINECO, Spain
Palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with in-situ generated 2-sodio-1,3-dithiane nucleophiles to afford the allylated products in good to excellent yields (25 examples). Deprotection of these products leads to valuable beta,gamma-unsaturated ketones. Direct synthesis of such beta,gamma-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Investigation into the stereochemistry of the allylation reaction revealed that the 2-sodio-1,3-dithiane nucleophile behaves as a soft nucleophile, which underwent external attack on the pi-allyl palladium complex to provide retention of stereochemistry (double inversion pathway). Additionally, the utility of this method was demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives, which are important bioactive compounds in medicinal chemistry.
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