The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(0) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.
Two step metal mediated Transformation of isoxazolidine-5-spirocyclopropanes into pyridone derivatives / J. REVUELTA; S. CICCHI; A. BRANDI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 70:(2005), pp. 5636-5642. [10.1021/jo050640q]
Two step metal mediated Transformation of isoxazolidine-5-spirocyclopropanes into pyridone derivatives.
REVUELTA CRESPO, JULIA MARIA;CICCHI, STEFANO;BRANDI, ALBERTO
2005
Abstract
The two-step metal-catalyzed overall transformation of isoxazolidine-5-spirocyclopropanes into the corresponding dihydro- and tetrahydropyridones is described. The first step is the chemoselective reduction of the N-O bond of the isoxazolidine ring preserving the fragile cyclopropanol moiety while the second transformation is the Pd(II) or Pd(0) conversion of the beta-aminocyclopropanol derivatives into the final compounds. The scope and limitations of this strategy are described.
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