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We are grateful to the Natural Sciences and Engineering Research Council of Canada for support of the research.
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Diastereoselective Synthesis of Hexahydropyrrolo[2,1-b]oxazoles by a Rhodium-Catalyzed Hydroformylation / Silica-Promoted Deformylation Sequence†
Article first published online: 12 JAN 2009
DOI: 10.1002/anie.200802550
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Vasylyev, M. and Alper, H. (2009), Diastereoselective Synthesis of Hexahydropyrrolo[2,1-b]oxazoles by a Rhodium-Catalyzed Hydroformylation / Silica-Promoted Deformylation Sequence. Angew. Chem. Int. Ed., 48: 1287–1290. doi: 10.1002/anie.200802550
- †
Publication History
- Issue published online: 28 JAN 2009
- Article first published online: 12 JAN 2009
- Manuscript Revised: 21 NOV 2008
- Manuscript Received: 1 JUN 2008
Funded by
- Natural Sciences and Engineering Research Council of Canada
Keywords:
- carbonylation;
- diastereoselectivity;
- heterocycles;
- hydroformylation;
- rhodium
Abstract
Fleetingly formyl: A new rhodium-catalyzed hydroformylation reaction of N-allyl oxazolidines, carried out under a CO/H2 atmosphere, followed by a diastereoselective deformylative cyclization affords hexahydropyrrolo[2,1-b]oxazoles in good yields. The reaction proceeds by a unique hydroformylation–deformylation sequence in which the formyl group virtually substitutes for the {CH2![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
O} fragment of the oxazolidine heterocycle.