1,3-Oxazin-2-ones vs tetrahydrofurans by iodocyclisation of 2-alkoxycarbonylamino-3-alken-1-ols

Joan Miquel Jordá-Gregori, Maria Eugenia González-Rosende, Patricia Cava-Montesinos, José Sepúlveda-Arques, Roberta Galeazzi, Mario Orena

Research output: Contribution to journalArticlepeer-review


Iodocyclisation of primary homoallylic alcohols 2a-d, containing either a 2-t-butoxy- or a benzyloxycarbonylamino group, was studied, in order to establish the nucleophilic group involved in cyclofunctionalisation. In fact, the N-t-Boc derivative 2a gave the oxazinone 3, exclusively, whereas starting from the N-Cbz derivative 2b a diastereomeric mixture of substituted tetrahydrofurans 4 and 5 resulted in ratios depending upon the reaction conditions. These results were rationalised by means of computational methods. On the contrary, migration of both the t-butyl or benzyl group to the hydroxy group was observed when both 2c and 2d underwent cyclisation to give the corresponding 5-alkoxymethyl oxazolidin-2-ones 7a,b in low yield, but with high regio- and stereocontrol. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3769-3777
Number of pages9
JournalTetrahedron: Asymmetry
Issue number18
Publication statusPublished - Sep 22 2000

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery


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