A versatile approach for the enantioselective synthesis of functionalised beta-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of the acyloxazolidone intermediate using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted gamma-lactones.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
Le Sann, C., Willis, C. L., Simpson, T. J., Watts, P., Munoz, D. M., Saunders, N., Smith, D. I., & Soulas, F. (2005). Assembly intermediates in polyketide biosynthesis; enantioselective syntheses of beta-hydroxycarbonyl compounds. Organic and Biomolecular Chemistry, 3 (9)(9), 1719-1728. https://doi.org/10.1039/b419492f