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. 2008 Jul 9;130(27):8602-3.
doi: 10.1021/ja803139k. Epub 2008 Jun 13.

One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles

James R Manning  1 , Huw M L Davies
Affiliations

One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles

James R Manning et al. J Am Chem Soc. .

Abstract

A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-dihydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general with a range of carbenoid and isoxazole components and represents a unique disconnection strategy for the synthesis of functionalized pyridines.

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