The development of iodo-arene containing peptides for the enantioselective α-oxytosylation of ketones has been explored.  A number of β-turn peptides bearing iodo-phenylalanine or capped with 2-iodobenzoic acid were synthesized and screened as catalysts for the enantioselective α-oxytosylation of ketones.  Catalytic reactions facilitated the α-oxytosylation of propiophenone with enantioselectivities up to 74:26 er, and the α-oxytosylation of indanone with enantioselectivities up to 82:18 er.  A series of stoichiometric reactions have been explored to probe the mechanism and stereochemical drivers governing the transformation.  A group of novel iodo-arene bearing amino acids have also been prepared.

Iodo-arene peptides for asymmetric hypervalent iodine chemistry

2019 Spring National Meeting

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