Literature DB >> 29504763

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

Jonathan M Ryss1, Amanda K Turek1, Scott J Miller1.   

Abstract

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.

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Year:  2018        PMID： 29504763      PMCID： PMC5963541          DOI： 10.1021/acs.orglett.8b00364

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

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  8 in total

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4.  Light-driven deracemization enabled by excited-state electron transfer.

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8.  Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.

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  8 in total

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