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Journal of Chemistry
Volume 2013, Article ID 349519, 5 pages
http://dx.doi.org/10.1155/2013/349519
Research Article

An Alternative Route for Synthesis of Chiral 4-Substituted 1-Arenesulfonyl-2-imidazolidinones: Unusual Utility of (4S,5S)- and (4R,5R)-4,5-Dimethoxy-2-imidazolidinones and X-Ray Crystallography

1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt
3Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt

Received 4 October 2013; Accepted 19 November 2013

Academic Editor: Narcis Avarvari

Copyright © 2013 Ibrahim A. Al-Swaidan et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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.