PALLADIUM-CATALYZED AEROBIC OXIDATION OF ALLYLIC AMINES VIA HETEROCYCLIC INTERMEDIATES
The efficient transformation of allylic amines into 2-amino-3-alken-1-ols and 1,2-diamino-3-alkenes is described.The key step is the functionalization of the ?-bond of the starting material via palladium(II)-mediated attack by an oxygen or nitrogen nucleophile, followed by palladium hydride elimination.When this reaction is carried out in DMSO as the solvent, molecular oxygen serves as a clean and efficient oxidant (without the need of a co-oxidant), thus making the process catalytic in palladium.By tethering the nucleophile to the nitrogen atom of the starting allylic amine, the intramolecular character of the key reaction ensures excellent regio- and stereoselectivity in several cases.The tether is readily removed by using an electrochemical oxidation and hydrolysis.
Hiemstra, Henk,Benthem, Rolf A. T. M. van
p. 559 - 564
(2007/10/02)
Synthesis of N-Boc-Protected 1-Amino-3-alken-2-ols from Allylic Carbamates via Palladium(II)-Catalyzed Oxidative Cyclization
Methyl glyoxylate adducts of N-Boc-protected allylic amines cyclize in the presence of catalytic Pd(OAc)2 and excess Cu(OAc)2 in DMSO to 5-(1-alkenyl)-2-(methyoxycarbonyl)oxazolidines.These heterocycles are readily converted to unsaturated.N-Boc-protected
Benthem, Rolf A. T. M. van,Hiemstra, Henk,Speckamp, W. Nico
p. 6083 - 6085
(2007/10/02)
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