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Enantioselective Functionalization of Enamides at the ?-Carbon Center with Indoles.

ABSTRACT: We report an enantioconvergent approach for the functionalization of enamides at the ?-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic ?-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.

SUBMITTER: Saputra MA 

PROVIDER: S-EPMC6407611 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles.

Saputra Mirza A MA   Nepal Binod B   Dange Nitin S NS   Du Pu P   Fronczek Frank R FR   Kumar Revati R   Kartika Rendy R  

Angewandte Chemie (International ed. in English) 20181023 47

We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner. ...[more]

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