Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acids.
[reaction: see text] Rhodium-catalyzed conjugate addition of an aryl boronic acid to alpha-methylamino acrylates followed by enantioselective protonation of the oxa-pi-allylrhodium intermediate provides access to aryl-substituted beta(2)-amino acids. The impact of the different variables of the reaction on the levels of enantioselectivity has been assessed.
Sibi
Mukund P
MP
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA. mukund.sibi@ndsu.edu
Tatamidani
Hiroto
H
Patil
Kalyani
K
D000179:Acrylates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000179:Acrylates; D000596:Amino Acids; D001897:Boronic Acids; D012238:Rhodium