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Issue 11, 2014
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Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

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Abstract

Chiral N,O-heterocycles were synthesized in high yields and excellent enantioselectivity up to 97% ee via iridium-catalysed intramolecular allylic substitution with nucleophilic attack by the amide oxygen atom. The resulting benzoxazine derivatives were further transformed into challenging chiral N,O-ketals bearing both a tertiary and a quaternary center with excellent diastereoselectivities.

Graphical abstract: Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

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Publication details

The article was received on 30 Jun 2014, accepted on 21 Jul 2014 and first published on 21 Jul 2014


Article type: Edge Article
DOI: 10.1039/C4SC01940G
Chem. Sci., 2014,5, 4216-4220
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

    D. Zhao, M. Fañanás-Mastral, M. Chang, E. Otten and B. L. Feringa, Chem. Sci., 2014, 5, 4216
    DOI: 10.1039/C4SC01940G

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