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

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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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This article has been cited by 22 ACS Journal articles (5 most recent appear below).

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Mechanisms of the Au- and Pt-Catalyzed Intramolecular Acetylenic Schmidt Reactions: A DFT Study

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