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.
|Number of pages||5|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - Jan 1 2000|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry