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A New Use of Wittig-Type Reagents as 1,3-Dipolar Cycloaddition Precursors and in Pyrrole Synthesis

Daniel J. St. Cyr and Bruce A. Arndtsen*

*Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 2K6, Canada, Email: bruce.arndtsenmcgill.ca

D. J. St. Cyr, B. A. Arndtsen, J. Am. Chem. Soc., 2007, 129, 12366-12367.

DOI: 10.1021/ja074330w (free Supporting Information)


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Abstract

A one-pot reaction of imines, acid chlorides, and phosphonites generates a new class of phosphorus-based 1,3-dipolar cycloaddition reagents. These substrates, which are isomeric forms of classic Wittig reagents, undergo cycloaddition reactions in an analogous fashion to 1,3-oxazolium-5-oxides (MŁnchnones).

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Key Words

1,3-dipolar cycloaddition, pyrroles


ID: J48-Y2007-3290