Abstract Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.
Bibliographical noteFunding Information:
The project described was supported in part by grant number R01- GM076192 from the National Institute of General Medicine . We thank National Science Foundation for grants to purchase the NMR spectrometer (CHE-9974801), and the mass spectrometer (CHE-9708640). We thank Mr. Joe Kramer and Prof. R.E.K. Winter of the Department of Chemistry and Biochemistry, UMSL for mass spectra.
© 2015 Elsevier Ltd.
- Allyl phosphonates
- Palladium π-allyl
- Vinyl phosphonates