Premium
Stereocontrolled Synthesis of Difunctionalized Azetidinones and β 2, 3 ‐Amino Acid Derivatives from Cyclodienes by Ring‐Opening and Cross‐Metathesis Reactions
Author(s) -
Kardos Márton,
Kiss Loránd,
Fülöp Ferenc
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500286
Subject(s) - chemistry , metathesis , ring (chemistry) , salt metathesis reaction , isocyanate , cycloaddition , amino acid , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , polymerization , polymer , biochemistry , polyurethane
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.