ol6b00108_si_002.cif (19.71 kB)
Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9‑(2-Tosylvinyl)‑9H‑purines
dataset
posted on 2016-02-04, 00:00 authored by Dan-Jie Zhang, Ming-Sheng Xie, Gui-Rong Qu, Yao-Wei Gao, Hai-Ming GuoWith 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.