STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-(3-ALKOXY AND 3-AMINOPROPANOYL)THIAZOLIDINE-2-THIONES STEREOSELECTIVE SYNTHESIS OF β-LACTAM DERIVATIVES

DOI: 10.1246/cl.1985.1045

Source and publish data:

Chemistry Letters p. 1045 - 1048 (1985)

Update date:2022-09-26

Topics:

Authors:

Iwasawa, Nobuharu

Huang, Huamin

Mukaiyama, Teruaki

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Article abstract of DOI:10.1246/cl.1985.1045

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.

Full text of DOI:10.1246/cl.1985.1045

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