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Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines

Authors

  • Jennifer Cockrell,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
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  • Christopher Wilhelmsen,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
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  • Heather Rubin,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
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  • Allen Martin,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
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  • Prof. Jeremy B. Morgan

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
    • Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
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  • The authors are grateful to the Donors of the American Chemical Society Petroleum Research Fund and UNCW for financial support. The Bruker NMR instrument used for 2D NMR studies was purchased with funds from the NSF (CHE-0821552). The HRMS data was collected by using a Bruker MicrOTOF-Q II purchased with funds from the NSF (CHE-1039784) and UNCW. We thank Jared Arnette for preliminary studies.

Abstract

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Die kinetische Racematspaltung von N-Acylaziridinen gelingt durch nucleophile Ringöffnung mit (R)-BINOL als chiralem Modifikator unter Bor-katalysierten Bedingungen (siehe Schema; Ar=3,5-Dinitrophenyl). Das verbrauchte Enantiomer des Aziridins kann zu einem enantiomerenangereicherten 1,2-Chloramid weiter umgesetzt werden, und (R)-BINOL wird zurückgewonnen.

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