An alternative route for synthesis of chiral 4-substituted 1-arenesulfonyl-2-imidazolidinones: Unusual utility of (4 S,5 S)- and (4 R,5 R)-4,5-dimethoxy-2-imidazolidinones and x-ray crystallography

Ibrahim A. Al-Swaidan, Amer M. Alanazi, Adel S. El-Azab, Alaa A.M. Abdel-Aziz

Research output: Contribution to journalJournal articlepeer-review

2 Scopus citations

Abstract

An unusual synthesis of (S)-1-arenesulfonyl-4-(1-adamantyl)-2- imidazolidinones 15a-d and (R)-1-arenesulfonyl-4-tert-butyl-2-imidazolidinones 19a-d has been developed from trans-1-apocamphanecarbonyl-4,5-dimethoxy-2- imidazolidinones 6 and 7 as chiral synthons. Diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully subjected to regioselective reduction using bulky organocuprates that afforded 1-apocamphanecarbonyl-5-methoxy-2-imidazolidinones 10 and 11. This new finding was used for synthesis of chiral 4-substituted 2-imidazolidinones 15a-d and 19a-d through the corresponding intermediates 13 and 17 by treatment with steric bulky tert-butylcuprate or 1-adamantylcuprate.

Original languageEnglish
Article number349519
JournalJournal of Chemistry
Volume2013
DOIs
StatePublished - 2013
Externally publishedYes

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