Premium
Site‐Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands
Author(s) -
Storch Golo,
Heuvel Naudin,
Miller Scott J.
Publication year - 2020
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.201900631
Subject(s) - chemistry , nitrene , oxazoline , polyene , peptide , combinatorial chemistry , conjugated system , bioconjugation , stereochemistry , covalent bond , substrate (aquarium) , selectivity , photochemistry , organic chemistry , catalysis , biochemistry , polymer , oceanography , geology
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.