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Armstrong A, Ferguson A. Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines. Beilstein J Org Chem. 2012;8:1747-52doi: 10.3762/bjoc.8.199.
Armstrong, A., & Ferguson, A. (2012). Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines. Beilstein journal of organic chemistry, 81747-52. https://doi.org/10.3762/bjoc.8.199
Armstrong, Alan, and Ferguson, Alexandra. "Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines." Beilstein journal of organic chemistry vol. 8 (2012): 1747-52. doi: https://doi.org/10.3762/bjoc.8.199
Armstrong A, Ferguson A. Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines. Beilstein J Org Chem. 2012;8:1747-52. doi: 10.3762/bjoc.8.199. Epub 2012 Oct 12. PMID: 23209508; PMCID: PMC3511008.
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Beilstein J Org Chem. 2012;8:1747-52. doi: 10.3762/bjoc.8.199. Epub 2012 Oct 12.

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines.

Beilstein journal of organic chemistry

Alan Armstrong, Alexandra Ferguson

Affiliations

  1. Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, U.K.

PMID: 23209508 PMCID: PMC3511008 DOI: 10.3762/bjoc.8.199

Abstract

tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N-N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles.

Keywords: amino acids; aziridination; organocatalysis; ring opening; stereoselectivity

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