title: Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides.
abstract: 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).
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
authors.forename: Naoki
authors.initials: N
authors.lastname: Ishida
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
authors.forename: David
authors.initials: D
authors.lastname: Nečas
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Masuda
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). murakami@sbchem.kyoto-u.ac.jp.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006037:Glyoxal / Q000138:chemical synthesis / Q000737:chemistry; D008027:Light; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000577:Amides; D010880:Piperidines; C062320:N-hydroxypiperidine; D006037:Glyoxal; D012238:Rhodium
keywords: CC activation; asymmetric synthesis; homogeneous catalysis; nitrogen heterocycles; rhodium