4.8 Article

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

期刊

CHEMICAL SCIENCE
卷 5, 期 11, 页码 4216-4220

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc01940g

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  1. Netherlands Organization for Scientific Research (NWO-CW)
  2. National Research School of Catalysis (NRSC-C)
  3. European Research Council (ERC) [227897]
  4. Royal Netherlands Academy of Arts and Sciences (KNAW)
  5. Ministry of Education Culture and Science [024.601035]

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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.

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