Related Experiment Videos
An olefin cross-metathesis approach to vinylphosphonate-linked nucleic acids
1The School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
Organic Letters
|August 17, 2001
Abstract:
[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).