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Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands.

Authors
  • Storch, Golo1
  • van den Heuvel, Naudin1
  • Miller, Scott J1
  • 1 Department of Chemistry, Yale University, New Haven, CT 06520-8107, USA.
Type
Published Article
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley
Publication Date
Jan 23, 2020
Volume
362
Issue
2
Pages
289–294
Identifiers
DOI: 10.1002/adsc.201900631
PMID: 32256275
Source
Medline
Keywords
Language
English
License
Unknown

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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