One-pot stereocontrolled cycloalkanone synthesis using 1,3-dithiane 1-oxides

✍ Scribed by Philip C. Bulman Page; Stephen J. Shutlleworth; Mark B. Schilling; David J. Tapolczay

• Book ID: 104224907
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 280 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91839-2

✦ Synopsis

Ldthium enolates of Zacyl-1,Sdithiane l-oxides, generated in one pot from 1.3-dithiane l-oxide, undergo highly diastereoselective alkylation upon treatment with alkyl iodide% similar In slfu treatment of these substrates with diiodoalkanes furnishes the corresponding medium-ring cycloalkanones with extremely high diastereoselectivity and in moderate to good yields.