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A Ring‐Closing Metathesis Approach to Cyclic α,β‐Dehydroamino Acids
Author(s) -
Hekking Koen F. W.,
Waalboer Dennis C. J.,
Moelands Marcel A. H.,
van Delft Floris L.,
Rutjes Floris P. J. T.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700308
Subject(s) - chemistry , ring closing metathesis , isomerization , allylic rearrangement , metathesis , ruthenium , salt metathesis reaction , hydride , olefin metathesis , acyclic diene metathesis , ring (chemistry) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , metal , polymerization , polymer
A comprehensive study on the synthesis and ring‐closing metathesis (RCM) of α,β‐dehydroamino acids is described. This sequence has led to the formation of a range of biologically relevant functionalized nitrogen heterocycles. The incorporation of chiral building blocks in the RCM precursors eventually resulted in the formation of optically active 4‐substituted cyclic dehydroamino acids. In addition, olefin isomerization under metathesis conditions was observed for a number of compounds, which could be successfully inhibited either by the introduction of allylic substituents or by the addition of a ruthenium hydride scavenger.