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Stereocontrolled Synthesis of Difunctionalized Azetidinones and β 2, 3 ‐Amino Acid Derivatives from Cyclodienes by Ring‐Opening and Cross‐Metathesis Reactions

2015; Wiley; Volume: 4; Issue: 10 Linguagem: Inglês

10.1002/ajoc.201500286

2193-5815

Márton Kardos, Lóránd Kiss, Ferenc Fülöp,

Synthesis and Catalytic Reactions

Abstract A stereocontrolled approach to highly functionalized 3,4‐disubstituted azetidin‐2‐ones and β 2, 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 β 2, 3 ‐amino acid derivatives.