Synfacts 2017; 13(01): 0043
DOI: 10.1055/s-0036-1589729
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Asymmetric Synthesis of α,α-Disubstituted Allylic N-Arylamines

Hisashi Yamamoto
Amit Banerjee
Cai A, Guo W, * Martínez-Rodríguez L, Kleij AW. * The Barcelona Institute of Science and Technology and Catalan Institute of Research and Advanced Studies, Barcelona, Spain
Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons.

J. Am. Chem. Soc. 2016;
138: 14194-14197
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19. Dezember 2016 (online)



The synthesis of α,α-disubstituted allylic amines is quite challenging. The authors report a palladium-catalyzed regio- and enantioselective allylic amination of vinyl cyclic carbonates with nonactivated aromatic amines to give the corresponding α,α-disubstituted allylic N-arylamines in good to excellent yields and high enantioselectivities.



The method is very simple and uses readily available starting materials. The amine products can serve as chiral building blocks for natural products and biologically active molecules.