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J Am Chem Soc. 2018 Mar 7;140(9):3177-3180. doi: 10.1021/jacs.7b12628. Epub 2018 Feb 7.

Lewis Base/Copper Cooperatively Catalyzed Asymmetric α-Amination of Esters with Diaziridinone.

Author information

1
Hefei National Laboratory for Physical Sciences at the Microscale, Department of Chemistry, and Center for Excellence in Molecular Synthesis of CAS , University of Science and Technology of China , Hefei 230026 , China.

Abstract

An enantioselective α-amination of esters by a Lewis base/copper(I) cooperative catalysis strategy has been developed. The transient chiral C1-ammonium enolate generated from pentafluorophenyl ester and nucleophilic Lewis base is nicely compatible with the copper intermediate formed from N, N-di- t-butyldiaziridinone and Cu(I) to allow for high levels of stereochemical control. The cooperative catalytic reaction leads to a diverse set of highly enantioenriched hydantoins in good yields with excellent enantioselectivities (90-99% ee).

PMID:
29377683
DOI:
10.1021/jacs.7b12628

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