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

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.

SUBMITTER: Armstrong A

PROVIDER: S-EPMC3511008 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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

Armstrong Alan A Ferguson Alexandra A

Beilstein journal of organic chemistry 20121012

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. ...[more]

PMID: 23209508

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