Tandem reformatsky reactions of 2-bromopropionates in the presence of chlorotrimethylsilane

✍ Scribed by Jacek K. Gawroński

• Book ID: 104233611
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 240 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81242-9

✦ Synopsis

Tandem aldol-like reactions are accessible through the addition of the Reformatsky reagent derived from 2-bromopropionate to either formate /eq 2/ or orthoformate /eq 3/ accep-tor in the presence of chlorotrimethylsilane. In recent years, as a result of extensive investigations, we have witnessed extraordinary progress in aldol reactions, especially in improving al-do1 stereoselection.' Despite of that, tandem enolate additions to a formate acceptor are quite uncommon, due to the expected interception of the initially formed aldehyde as a stable metal enolate.