Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis

作者:Ryss Jonathan M; Turek Amanda K; Miller Scott J*
来源:Organic Letters, 2018, 20(6): 1621-1625.
DOI:10.1021/acs.orglett.8b00364

摘要

An enantioselective vinylcyclopropane ring-opening/cycloaddition cascade is described. The active thiyl radical catalysts are generated in situ via UV light-promoted homolysis of cystine-based dimers. Amide-functionalization of the peptide at the 4-proline position is essential for effective asymmetric induction. Stereochemical communication is dependent on steric interactions with this substituent that are enforced by H-bonding to the peptide backbone.

  • 出版日期2018-3-16