4.8 Article

Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 25, Pages 7418-7421

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502584

Keywords

asymmetric synthesis; C-C activation; homogeneous catalysis; nitrogen heterocycles; rhodium

Funding

  1. MEXT
  2. JST
  3. Grants-in-Aid for Scientific Research [24655077, 14J03286] Funding Source: KAKEN

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3-Hydroxypiperidine scaffolds were enantioselectively constructed in an atom-economical way by sequential action of light and rhodium upon N-allylglyoxylamides. In a formal sense, the allylic C-H bond was selectively cleaved and enantioselectively added across the ketonic carbonyl group with migration of the double bond (carbonyl-ene-type reaction).

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