Nucleoside analog-based phosphonates via photochemical, single electron transfer (SET) induced rearrangements of allyl phosphites

Article abstract of DOI:10.1016/S0040-4039(97)10678-5

The photochemical SET rearrangement of nucleoside analog-based phosphites 12 and 13, initiated by the singlet excited state of DCN, affords the corresponding diethyl phosphonates 14 and 15. Deprotection of 15 gives phosphonate 16. Treatment of 14 - 16 with base yields the vinylphosphonates 17-19 as the (E)- and (Z)-diastereomers.