Palladium(II)-catalyzed coupling of allenoic acids and α,β-unsaturated carbonyl compounds through tandem intramolecular oxypalladation and conjugate addition reactions
✍ Scribed by Guosheng Liu; Xiyan Lu
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 248 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A regioselective divalent palladium-catalyzed tandem coupling reaction of allenoic acids with a,b-unsaturated carbonyl compounds was developed. The reaction involves intramolecular oxypalladation of an allene, followed by insertion of the a,b-unsaturated carbonyl compound and protonolysis of the C Pd bond to regenerate the Pd(II) species in the presence of excess halide ions. Functionalized lactones, tetrahydropyranones and dihydropyranones can be synthesized with high regioselectivity in one step.
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