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Beilstein J. Org. Chem. 2014, 10, 1933–1941, doi:10.3762/bjoc.10.201
Graphical Abstract
Scheme 1: Palladium catalysed reaction of phosphono allylic carbonates.
Figure 1: Natural products prepared using vinyl phosphonate intermediates.
Scheme 2: Approaches to the synthesis of centrolobine.
Scheme 3: Relay ring closing metathesis and relay cross metathesis.
Scheme 4: Cross metathesis reactions of vinyl phosphonates.
Scheme 5: Transesterification of phosphonate esters.
Scheme 6: Relay cross metathesis of mono-allyl vinylphosphonates with methyl acrylate.
Scheme 7: Relay cross metathesis of mono-allyl vinylphosphonates with styrenes.
Scheme 8: Ring closing vs relay cross metathesis.
Scheme 9: Relay cross metathesis of diallyl vinylphosphonates with methyl acrylate.
Scheme 10: A cross metathesis reaction of both mono- and diallyl vinylphosphonates with methyl acrylate.
Scheme 11: A proposed mechanism for the relay cross metathesis reaction of allyl vinylphosphonates.
Scheme 12: A proposed mechanism for the TBAI catalysed transesterification.
Scheme 13: A selective synthesis of mono-allyl phosphonates.