Dynamic kinetic asymmetric allylation of hydrazines and hydroxylamines.
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.
Mangion
Ian
I
Merck Research Laboratories, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. ian_mangion@merck.com
Strotman
Neil
N
Drahl
Michael
M
Imbriglio
Jason
J
Guidry
Erin
E
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
D000588:Amines; D006834:Hydrazines; D006898:Hydroxylamines; D011724:Pyridazines; C014756:piperazic acid; D010165:Palladium