Direct conversion of esters to secondary amides using tin(II) reagents

✍ Scribed by Wei-Bo Wang; José A. Restituyo; Eric J. Roskamp

• Book ID: 104215902
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 267 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79291-4

✦ Synopsis

We have developed two new procedmea for the dtrect converston of e&are to secondary am&b. In our first procedure, secondary amides can be prepared in 8348% yield starting from glycol esters. Addition of Sn[NU'MS)~2 and a primary amine to the glycol ester generates an intermediate tin(III alkoxy amide, which delivem the amino group intramolecularly to give the amide. A second general @we for the preparation of secondary amides starts with methyl esters. Treatment of methyl esters with a tin reagent derived from SnINRMS)~~ eNCH$ZHflH, and a primary amine yields secondary amides in 8748% yield.