We acknowledge support from the EPSRC and GlaxoSmithKline (S.P.), and from the Ministerio de Educación of Spain (N.C.). We are grateful to Tom Baker and Ol'ga Karlubíková for synthetic assistance.
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Communication
Stereoselective Dearomatizing Addition of Nucleophiles to Uncomplexed Benzene Rings: A Route to Carbocyclic Sugar Analogues†
Article first published online: 2 JUN 2008
DOI: 10.1002/anie.200801078
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Clayden, J., Parris, S., Cabedo, N. and Payne, Andrew H. (2008), Stereoselective Dearomatizing Addition of Nucleophiles to Uncomplexed Benzene Rings: A Route to Carbocyclic Sugar Analogues. Angew. Chem. Int. Ed., 47: 5060–5062. doi: 10.1002/anie.200801078
- †
Publication History
- Issue published online: 16 JUN 2008
- Article first published online: 2 JUN 2008
- Manuscript Received: 5 MAR 2008
Funded by
- EPSRC
- GlaxoSmithKline
- Ministerio de Educación of Spain
Keywords:
- carbohydrates;
- dearomatization;
- diastereoselectivity;
- oxazolines;
- pseudosugars
Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.