Metal directed stereoselective synthesis of 3-(1′-hydroxyethyl)-2-azetidinones from ethyl 3-hydroxybutyrate

Gunda I. Georg, Eyüp Akgün

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10.

Original languageEnglish (US)
Pages (from-to)3267-3270
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number23
DOIs
StatePublished - 1990

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