title: Raney-Co mediated reductive cyclization of an alpha,beta-unsaturated nitrile.
abstract: An expedient, five step synthesis of caprolactam 1 is reported starting from natural L-homoserine. The key step is a chemoselective reductive cyclization of alpha,beta-unsaturated nitrile 10 mediated by Raney-Co type metals. This hydrogenation is extensively investigated in order to account for the observed product distribution and yields.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Merck and Co., Inc., Rahway, New Jersey 07065, USA. jacob_janey@merck.com
authors.forename: Jacob M
authors.initials: JM
authors.lastname: Janey
authors.forename: Charles J
authors.initials: CJ
authors.lastname: Orella
authors.forename: Eugenia
authors.initials: E
authors.lastname: Njolito
authors.forename: Jenny M
authors.initials: JM
authors.lastname: Baxter
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Rosen
authors.forename: Michael
authors.initials: M
authors.lastname: Palucki
authors.forename: Rick R
authors.initials: RR
authors.lastname: Sidler
authors.forename: Wenjie
authors.initials: W
authors.lastname: Li
authors.forename: Jason J
authors.initials: JJ
authors.lastname: Kowal
authors.forename: Ian W
authors.initials: IW
authors.lastname: Davies
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002209:Caprolactam / Q000737:chemistry; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D006714:Homoserine / Q000138:chemical synthesis / Q000737:chemistry; D007536:Isomerism; D008715:Methionine / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013696:Temperature
chemical_list: D000447:Aldehydes; D009570:Nitriles; D003035:Cobalt; D002209:Caprolactam; D006714:Homoserine; D008715:Methionine