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Carbonylative Ring Opening of Terminal Epoxides at Atmospheric Pressure

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Scott E. Denmark* and Moballigh Ahmad

Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801

J. Org. Chem., 2007, 72 (25), pp 9630–9634

DOI: 10.1021/jo7014455

Publication Date (Web): November 8, 2007

Section:

Aliphatic Compounds

Abstract

The carbonylative opening of terminal epoxides under mild conditions has been developed using Co₂(CO)₈ as the catalyst. Under 1 atm of carbon monoxide and at room temperature in methanol, propylene oxide is converted to methyl 3-hydroxybutanoate in up to 89% yield. This transformation is general for many terminal epoxides bearing alkyl, alkenyl, aryl, alkoxy, chloromethyl, phthalimido, and acetal functional groups. The opening takes place without epimerization at the secondary stereocenter.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

In Situ Generation of the Coates Catalyst: A Practical and Versatile Catalytic System for the Carbonylation of meso-Epoxides
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Organic Letters2011 Article ASAP
- In Situ Generation of the Coates Catalyst: A Practical and Versatile Catalytic System for the Carbonylation of meso-Epoxides
  Prasad Ganji, David J. Doyle, and Hasim Ibrahim
  Organic Letters2011 Article ASAP
  A highly active catalytic system for the carbonylation of meso- and terminal epoxides to β-lactones is described. The active catalyst, analogous to Coates’ catalyst, is generated in situ from commercially available (TPP)CrCl and Co2(CO)8. This practical ...
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Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid
Steven M. Raders and John G. Verkade
The Journal of Organic Chemistry2009 74 (15), 5417-5428
- Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid
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  The Journal of Organic Chemistry2009 74 (15), 5417-5428
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  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links