Diastereoselective addition of a silylketene acetal to chiral α-thioaldehydes.

✍ Scribed by Rita Annunziata; Mauro Cinquini; Franco Cozzi; Pier Giorgio Cozzi

• Book ID: 104228453
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 197 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97160-0

✦ Synopsis

Chirala-thioaldehydes 2-6 undergo chelation or non-chelation controlled addition of silylketene acetal 1, depending on the nature of the Lewis acid catalyst and of the ligands at the stereocenter. Lewis acid (L.a.) promoted addition of silyl enolethers and silylketene acetals to aldehydes represents an efficient alternative to the classic aldol condensation.' This methodology can