STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-(3-ALKOXY AND 3-AMINOPROPANOYL) THIAZOLIDINE-2-THIONES STEREOSELECTIVE SYNTHESIS OF β-LACTAM DERIVATIVES
- Resource Type
- Article
- Authors
- Iwasawa, Nobuharu; Huang, Huamin; Mukaiyama, Teruaki
- Source
- Chemistry Letters; July 1985, Vol. 14 Issue: 7 p1045-1048, 4p
- Subject
- Language
- ISSN
- 03667022; 13480715
The tin(II) enolate is generated from 3-acylthiazolidine-2-thione with β-alkoxy or β-amino functionality on treatment with stannous triflate in the presence of N-ethylpiperidine. The enolate further reacts with aldehyde to afford the aldol product with high syn-stereoselectivity. The aldol product thus produced is stereospecifically converted to β-lactam derivative with hydroxyethyl side chain.