The synthesis of novel C 2 -symmetric 1,3-imidazolidinones (II) as bifunctional chiral auxiliaries from enantiomerically pure compound (I), a chiral waste in the synthetic process of D-biotin, is described.
Bifunctional chiral auxiliaries 2: the synthesis of 1,3-diacylimidazolidin-2-ones from 1,2-diamines
β Scribed by Stephen G. Davies; Andrew A. Mortlock
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 287 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The final step involves the novel use of mercury (II) acetate for the conversion of thioureas to ureas.
Our desire to develop a novel series of bifunctional chiral auxiliaries, requires the synthesis of C2 symmetric 1,3-diacylimidazolidin-2-onesl.
The availability of truns-1,2diamines such as trans-1,2-diaminocyclohexane la2 and fruns-1,2-diphenyl-1,Zdiarninoethane lb3, coupled with the ease of their resolution4, indicated their suitability as starting materials for such a synthesis. Such an approach would therefore be analogous to the
π SIMILAR VOLUMES
Addition of alkyl halides to sodium and potassium enolates of 1,3-diacyl-trans-4,5-