title: Dynamic kinetic asymmetric allylation of hydrazines and hydroxylamines.
abstract: Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.
authors: Merck Research Laboratories, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. ian_mangion@merck.com
authors: Ian
authors: I
authors: Mangion
authors: Neil
authors: N
authors: Strotman
authors: Michael
authors: M
authors: Drahl
authors: Jason
authors: J
authors: Imbriglio
authors: Erin
authors: E
authors: Guidry
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry*; D007700:Kinetics; D010165:Palladium / Q000737:chemistry; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D006834:Hydrazines; D006898:Hydroxylamines; D011724:Pyridazines; C014756:piperazic acid; D010165:Palladium