Synthesis of chiral pyrimidine-substituted diester D-A cyclopropanes via asymmetric cyclopropanation of phenyliodonium ylides.
Hai-Xia WangWen-Peng LiMi-Mi ZhangMing-Sheng XieGui-Rong QuHai-Ming GuoPublished in: Chemical communications (Cambridge, England) (2020)
A highly enantioselective cyclopropanation to synthesize pyrimidine-substituted diester D-A cyclopropanes is reported. Various N1-vinylpyrimidines react well with phenyliodonium ylides, delivering chiral cyclopropanes in up to 97% yield with up to 99% ee. Through simple [3+2] annulation with benzaldehyde or ethyl glyoxylate, different chiral pyrimidine nucleoside analogues with a sugar ring could be obtained.