Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 14, Pages 5846-5849Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2006363
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- Universite de Montreal
- Fonds Quebecois de la Recherche sur la Nature et les Technologies (FQRNT)
- Natural Science and Engineering Research Council of Canada (NSERC)
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Peptide mimics with constrained backbone and side-chain geometry are important tools for studying structure activity relationships of biologically active candidates. A general method for creating beta-turn mimics possessing side-chain diversity has been developed featuring diastereoselective S(N)1 displacements of an iodide precursor. In particular, 6-iodo-pyrroloazepin-2-one amino ester 10 has served as a common precursor in reactions with a variety of alcohol, phenol, nitrate, and azide nucleophiles to provide an array of constrained peptide mimics.
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