Stereocontrolled synthesis of difunctionalized azetidinones and β2,3-amino acid derivatives from cyclodienes by ring opening and cross-metathesis reactions

Kardos, Márton and Kiss, Loránd and Fülöp, Ferenc (2015) Stereocontrolled synthesis of difunctionalized azetidinones and β2,3-amino acid derivatives from cyclodienes by ring opening and cross-metathesis reactions. Asian Journal of Organic Chemistry. pp. 1155-1159.

Text AJOC20150001.pdf Restricted to Registered users only Download (3MB)

Abstract

A stereocontrolled approach to novel highly functionalized 3,4-disubstituted azetidin-2-ones and β2,3-amino acid derivatives from readily available cycloalkadienes was achieved. The syntheses involved 1,3-dipolar cycloaddition of chlorosulfonyl isocyanate, followed by ring opening metathesis of the unsaturated bi- or tricyclic β-lactams, and cross-metathesis of the resulting divinyl-substituted azetidinones. The substituted lactams were subsequently transformed by heteroring opening into the corresponding functionalized acyclic β2,3-amino acid derivatives.

Actions (login required)

Edit Item