Reaction of 1,3-disubstituted acetone derivatives with pseudohalides: A simple approach to spiro[4.4]nonane-Type bis-oxazolidines and -imidazolidines (bicyclic carbamates, thiocarbamates, ureas, and thioureas)

Robert Saul, Thorsten Kern, Jürgen Kopf, István Pintér, Peter Köll

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Prochiral 1,3-dihydroxyacetone forms racemic oxazolidine- and oxazoline- type spiro[4.4]nonanes upon reactions with potassium (thio)cyanate and cyanamide. In contrast, 1,3-diaminoacetone yields only the corresponding spirobisimidazolidinethione under similar conditions together with monocyclic by-products, but the spirobisimidazolidinone is accessible by reaction of 1,3-dichloroacetone with urea. The resolution of the racemic spiro- bisoxazolidinethione 2a was achieved by using brucine as the resolving agent.

Original languageEnglish
Pages (from-to)205-209
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number1
Publication statusPublished - Jan 1 2000

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Keywords

  • Carbohydrates
  • Heterocycles
  • Imidazolidines
  • Oxazolidines
  • Spiro[4.4]nonanes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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