Synthesis of chiral pyrimidine-substituted diester D–A cyclopropanes via asymmetric cyclopropanation of phenyliodonium ylides

Synthesis of chiral pyrimidine-substituted diester D–A cyclopropanes via asymmetric cyclopropanation of phenyliodonium ylides

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 benzald...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-10, Vol.56 (78), p.11649-11652
Hauptverfasser: Wang, Hai-Xia, Li, Wen-Peng, Zhang, Mi-Mi, Xie, Ming-Sheng, Qu, Gui-Rong, Guo, Hai-Ming
Format: Artikel
Sprache:eng
Schlagworte:
Benzaldehyde
Chemical reactions
Crystallography
Diesters
Enantiomers
Organic compounds
Substitutes
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04536e