Metallation reactions. XXXIV. Synthesis of 2-(1-hydroxy-1-arylethyl)-1,3-benzoxathiol-3-oxide derivatives

✍ Scribed by Salvatore Cabiddu; Enzo Cadoni; Stefana Melis; Alen Ianni; Angela M. Bernard; Maria G. Cabiddu; Stefania De Montis; Claudia Fattuoni; Sandra Ianelli

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 129 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400605

✦ Synopsis

Abstract

The reaction of benzoxathiole‐3‐oxide with lithiumdiisopropylamide in tetrahydrofuran gave an anion, which was reacted with various aryl‐methyl‐ketones to give 2‐(1‐hydroxy‐1‐arylethyl)‐1,3‐benzoxathiol‐3‐oxide derivatives. The reaction was carried out in different temperature conditions: at ‐88 °C the trans addition stereoisomers to the sulfoxide oxygen atom were the main products.