Enantioselective Rhodium Enolate Protonations. A New Methodology for the Synthesis of Beta2-amino Acids
Overview
Chemistry
Affiliations
[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.
Palillero-Cisneros A, Gordillo-Guerra P, Garcia-Alvarez F, Jackowski O, Ferreira F, Chemla F Beilstein J Org Chem. 2023; 19:1443-1451.
PMID: 37767333 PMC: 10520473. DOI: 10.3762/bjoc.19.103.
Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride.
Gu Y, Norton J, Salahi F, Lisnyak V, Zhou Z, Snyder S J Am Chem Soc. 2021; 143(25):9657-9663.
PMID: 34142805 PMC: 9366878. DOI: 10.1021/jacs.1c04683.
Conjugate addition-enantioselective protonation reactions.
Phelan J, Ellman J Beilstein J Org Chem. 2016; 12:1203-28.
PMID: 27559372 PMC: 4979737. DOI: 10.3762/bjoc.12.116.
Gigant N, Quintin F, Backvall J J Org Chem. 2015; 80(5):2796-803.
PMID: 25653084 PMC: 4354172. DOI: 10.1021/acs.joc.5b00148.
Filloux C, Rovis T J Am Chem Soc. 2014; 137(1):508-17.
PMID: 25545834 PMC: 4304441. DOI: 10.1021/ja511445x.