Get access

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)
    Search for more papers by this author
  • Christopher Wilhelmsen,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
    Search for more papers by this author
  • Heather Rubin,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
    Search for more papers by this author
  • Allen Martin,

    1. Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, NC 28403 (USA)
    Search for more papers by this author
  • 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)
    Search for more papers by this author

  • 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

original image

Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL.

Ancillary