Highly Enantioselective Decarboxylative Protonation of α-Aminomalonates Mediated by Thiourea Cinchona Alkaloid Derivatives: Access to Both Enantiomers of Cyclic and Acyclic α-Aminoacids
- 19 June 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (14) , 2621-2624
- https://doi.org/10.1021/ol070712v
Abstract
Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer 6 derived from quinine.Keywords
This publication has 11 references indexed in Scilit:
- Inversion of enantioselectivity of arylmalonate decarboxylase via site-directed mutation based on the proposed reaction mechanismJournal of Molecular Catalysis B: Enzymatic, 2006
- Organocatalysis Mediated by (Thio)urea DerivativesChemistry – A European Journal, 2006
- Mechanism of asymmetric decarboxylation of α-aryl-α-methylmalonate catalyzed by arylmalonate decarboxylase originated from Alcaligenes bronchisepticusJournal of Molecular Catalysis B: Enzymatic, 2004
- Enzyme-mediated asymmetric decarboxylation of disubstituted malonic acidsJournal of the American Chemical Society, 1990
- Asymmetric synthesis by copper-catalyzed decarboxylation of phenylmalonic diacids and hemiestersTetrahedron Letters, 1987
- Mechanism for chiral recognition of a prochiral center and for asymmetric induction in asymmetric syntheses of .alpha.-amino acids using chiral cobalt(III) complexes. Crystal and molecular structures of (.alpha.-amino-.alpha.-methylmalonato)(4,6-dimethyl-1,9-diamino-3,7-diazanonane)cobalt perchlorate monohydrate and (.alpha.-amino-.alpha.-methylmalonato)(6,8-dimethyl-2,5,9,12-tetraazatridecane)cobalt bromide trihydrateInorganic Chemistry, 1986
- Asymmetric decarboxylation of ethylphenylmalonic acid in a cholesteric liquid crystal solventThe Journal of Organic Chemistry, 1975
- Mechanism for chiral recognition of a prochiral center and for amino acid complexation to a cobalt(III) tetramine. Crystal structure, absolute configuration, and circular dichroism of .lambda.(-)436-.beta.-2-[(2S,9S)-2,9-diamino-4,7-diazadecanecobalt(III) aminomethylmalonate] perchlorate monohydrateJournal of the American Chemical Society, 1974
- Ueber asymmetrische SyntheseEuropean Journal of Inorganic Chemistry, 1904
- Ueber asymmetrische SyntheseEuropean Journal of Inorganic Chemistry, 1904