Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands
Golo Storch1, Naudin van den Heuvel1, Scott J Miller1
1Department of Chemistry, Yale University, New Haven, CT 06520-8107, USA.
Abstract:
Site-selective nitrene transfer to di- and polyene substrates has been achieved using designed peptide-embedded bioxazoline ligands capable of binding copper. In model 1,3-diene substrates, the olefinic position proximal to a directing group was selectively functionalized. Additional studies indicate that this selectivity stems from non-covalent substrate-catalyst interactions. The peptide-mediated nitrene transfer was also applied to polyene natural product retinol and selective proximal functionalization allowed access to a cis-pyrroline modified retinoid.
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