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Heterocycles from Unsaturated Phosphorus Ylides

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Book cover Synthesis of Heterocycles via Cycloadditions I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 12))

Abstract

Phosphacumulene ylides of the general formula Ph3P=C=C=X [X=O, S, NR, (OR)2] are versatile C2-building blocks. They can act either as C-nucleophiles-only in a manner typical of phosphorus ylides, or as cumulenes undergoing [2 + n]-cycloadditions with other cumulenes such as CO2, COS, RNCO etc. Most prominent is their tandem addition–Wittig alkenation of hydroxy- or amino-substituted carbonyl compounds. With aptly chosen reaction partners all these pathways may lead to heterocyclic products. Some recent applications of these methods to the syntheses of azetidines, five-membered lactams, lactones, tetramates, tetronates and pyrroles as well as to six-membered quinolones and to macrolides are delineated.

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Authors and Affiliations

  1. Organic Chemistry Laboratory, University of Bayreuth, NW I, Universitätsstr. 30, 95440, Bayreuth, Germany

    Rainer Schobert & Claus Hölzel

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  1. Rainer Schobert
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  2. Claus Hölzel
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Correspondence to Rainer Schobert .

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Alfred Hassner

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Schobert, R., Hölzel, C. (2007). Heterocycles from Unsaturated Phosphorus Ylides. In: Hassner, A. (eds) Synthesis of Heterocycles via Cycloadditions I. Topics in Heterocyclic Chemistry, vol 12. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_097

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