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
Key words
palladium - vinylic cyclic carbonates - allylic amines - tertiary stereocenters
Significance
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.
Comment
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.
