An olefin cross-metathesis approach to vinylphosphonate-linked nucleic acids.
[reaction: see text]. The synthesis of vinylphosphonate-linked nucleotide dimers has been achieved using an olefin cross-metathesis (CM) reaction as a key step. The 1,3-dimesityl-4,5-dihydroimidazol-2-ylidine-containing catalyst 5 (Grubbs' second-generation catalyst) was found to be the superior catalyst for this transformation. Both metathesis partners were readily available using known methodology, and the vinylphosphonate-linked dimer was produced with high levels of (E)-selectivity (>20:1) in 58% yield (70% based on recovered starting material).
Lera
M
M
The School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
Hayes
C J
CJ
D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D009696:Nucleic Acids; D063065:Organophosphonates; D014753:Vinyl Compounds