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

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-oxazoli...

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Veröffentlicht in:Journal of the American Chemical Society 2007-10, Vol.129 (41), p.12366-12367
Hauptverfasser: St. Cyr, Daniel J, Arndtsen, Bruce A
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja074330w