A New Use of Wittig-Type Reagents as 1,3-Dipolar Cycloaddition Precursors and in Pyrrole Synthesis
Journal of the American Chemical Society2007Vol. 129(41), pp. 12366–12367
Citations Over TimeTop 10% of 2007 papers
Abstract
The one-pot reaction of imines, acid chlorides, and phosphonites has been found to generate a new class of phosphorus-based 1,3-dipolar cycloaddition reagent. These substrates, which are isomeric forms of classic Wittig reagents, undergo cycloaddition reactions in an analogous fashion to 1,3-oxazolium-5-oxides (Münchnones). However, these 1,3-dipoles can be generated in one pot, in a modular fashion, and directly from available reagents, suggesting their potential general utility in heterocycle synthesis. The latter is illustrated in the design of a phosphonite-mediated synthesis of pyrroles from a variety of imines, acid chlorides, and alkynes.
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