Back to Search
Start Over
Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9-(2-Tosylvinyl)-9H-purines.
- Source :
-
Organic Letters . Feb2016, Vol. 18 Issue 4, p820-823. 4p. - Publication Year :
- 2016
-
Abstract
- With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were obtained in 86-99% yields, >20:1 dr, and 94 → 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when α-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 18
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 113570820
- Full Text :
- https://doi.org/10.1021/acs.orglett.6b00108