Sulfenylated cyclic β-keto esters and cyclic β-diketones; synthesis and reactions with nucleophiles

✍ Scribed by Ae. de Groot; B. J. M. Jansen

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 617 KB
• Volume: 98
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19790980904

✦ Synopsis

Abstract

Quenching the enolates of cyclic β‐diketones or 2‐oxocycloalkanecarboxylates with phenylsulfenyl chloride or methylsulfenyl chloride produces the corresponding x‐sulfenylated products. Nucleophilic attack on these x‐sulfenylated 1,3‐dicarbonyl compounds produces regiospecific sulfenylated linear dicarboxylic acids, acid esters, diesters or oxo esters suitable for further chemical transformation, this has been demonstrated in the synthesis of the queen substance of the honoy bee. In some cases recyclization of the intermediate enolates was observed to regiospecific sulfenylated cyclohexenones.