Palladium-catalyzed asymmetric allylic amination of a vinylethylene carbonate with N-heteroaromatics
- Resource Type
- Authors
- Gui-Rong Qu; Dong-Chao Wang; Hai-Ming Guo; Chao Xia
- Source
- Organic Chemistry Frontiers. 8:2569-2575
- Subject
- inorganic chemicals
Allylic rearrangement
010405 organic chemistry
organic chemicals
Acyclic nucleoside
Organic Chemistry
Enantioselective synthesis
chemistry.chemical_element
010402 general chemistry
01 natural sciences
Combinatorial chemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Carbonate
Amination
Palladium
- Language
- ISSN
- 2052-4129
Highly enantioselective allylation of a vinylethylene carbonate by asymmetric palladium catalysis has been developed for a variety of N-heteroaromatic substrates. The employed procedure allows for the efficient synthesis of various acyclic nucleoside analogs in good yields (up to 96%) and with high enantioselectivities (up to 99%) at the Pd catalyst amount of 0.5 mol%. In addition, these acyclic nucleosides are demonstrated to undergo rapid transformation to a variety of interesting structurally diverse chiral acyclic nucleosides and isonucleosides.