NUCLEOSIDE ANALOG-BASED PHOSPHONATES VIA PHOTOCHEMICAL, SINGLE-ELECTRON TRANSFER (SET) INDUCED REARRANGEMENTS OF ALLYL PHOSPHITES

Authors
JEON GS BENTRUDE WG
Citation
Gs. Jeon et Wg. Bentrude, NUCLEOSIDE ANALOG-BASED PHOSPHONATES VIA PHOTOCHEMICAL, SINGLE-ELECTRON TRANSFER (SET) INDUCED REARRANGEMENTS OF ALLYL PHOSPHITES, Tetrahedron letters, 39(9), 1998, pp. 927-930
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
9
Year of publication
1998
Pages
927 - 930
Database
ISI
SICI code
0040-4039(1998)39:9<927:NAPVPS>2.0.ZU;2-B
Abstract
The photochemical SET rearrangement of nucleoside analog-based phosphi tes 12 and 13, initiated by the singlet excited state of DCN, affords the corresponding diethyl phosphonates 14 and 15. Deprotection of 15 g ives phosphonate 16. Treatment of 14 - 16 with base yields the vinylph osphonates 17-19 as the (E)- and (Z)-diastereomers. (C) 1998 Elsevier Science Ltd. All rights reserved.