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Expedient Pathway into Optically Active 2‐Oxopiperidines
Author(s) -
van den Broek Sebastiaan Bas A. M. W.,
Rensen Peter G. W.,
van Delft Floris L.,
Rutjes Floris P. J. T.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000587
Subject(s) - piperidine , chemistry , pipecolic acid , ring (chemistry) , ring closing metathesis , metathesis , combinatorial chemistry , stereochemistry , optically active , salt metathesis reaction , organic chemistry , amino acid , biochemistry , polymerization , polymer
Abstract The piperidine ring system is one of the most common structural subunits and is found in many natural products. Moreover, piperidine alkaloids and derivatives thereof are of great interest for the pharmaceutical industry since they exhibit a wide range of biological activities. Consequently, short and valuable routes to highly functionalized building blocks for this important ring system are of general interest. A ring‐closing metathesis (RCM)‐mediated approach based on linear (substituted) dehydroamino esters was developed to provide cyclic dehydroamino esters. These structures represent valuable intermediates en route to highly substituted pipecolic acids as well as more elaborate heterocycles.