Nitrogen Heterocycles From Furans: The Aza-Achmatowicz Reaction

Marco A. Ciufolini; Cynthia Y. W. Hermann; Qing Dong; Toshio Shimizu; Shankar Swaminathan; Ning Xi

doi:10.1055/s-1998-1584

Synlett 1998; 1998(2): 105-114
DOI: 10.1055/s-1998-1584

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Nitrogen Heterocycles From Furans: The Aza-Achmatowicz Reaction

Marco A. Ciufolini^* , Cynthia Y. W. Hermann, Qing Dong, Toshio Shimizu, Shankar Swaminathan, Ning Xi

^*Department of Chemistry, MS 60, Rice University, 6100 Main, Houston, TX 77005-1892, U.S.A.; Fax [int] (713) 2 85-51 55; E-mail: ciufi@ruf.rice.edu

Abstract

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The furan nucleus may be considered as a latent 1,4-dicarbonyl group. Expression of this functional equivalence within a generic 2-furylamide results in formation of nitrogen heterocycles in a reaction that may be termed the "Aza-Achmatowicz rearrangement", by analogy with similar transformations of furylcarbinols. Aza-Achmatowicz products may be created in enantioselective form by chemoenzymatic methods, and are useful intermediates in the synthesis of novel carbacephems, unusual aminoacids, azasaccharides, piperidine and izidine alkaloids. This Account reviews the most significant aspects of aza-Achmatowicz chemistry.

alkaloids - aminoacids - azasaccharides - carbacephems - enzymes - furans - izidines - piperidines

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