Abstract
Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.
Original language | English (US) |
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Pages (from-to) | 1768-1771 |
Number of pages | 4 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 18 |
Issue number | 6 |
DOIs | |
State | Published - Mar 15 2008 |
Keywords
- Asymmetric
- Enolate
- Heterocycle
- Thiazolidinedione
- Thiocyanate
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry