Synfacts 2007(9): 0978-0978  
DOI: 10.1055/s-2007-968821
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Multicomponent Reaction of Epoxides, Isocyanates, and CO

Contributor(s): Paul Knochel, Andrei Gavryushin
T. L. Church, C. M. Byrne, E. B. Lobkovsky, G. W. Coates*
Cornell University, Ithaca, USA
Further Information

Publication History

Publication Date:
23 August 2007 (online)

Significance

The authors developed a new elegant and synthetically useful stereoselective transition-metal-catalyzed multicomponent reaction, yielding 1,3-oxazinane-2,4-diones from readily available epoxides and isocyanates. The products are valuable synthetic intermediates for the preparation of β-hydroxypropionic acids, 1,3-diols, substituted acrylic acids, etc. Cyclic epoxides, which are usually difficult to carbonylate, can be readily involved in this process. The reaction is especially smooth in the case of aryl isocyanates.