Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.
The highly chemo- and enantioselective organocatalytic tandem reaction between N-protected hydroxyl amines and alpha,beta-unsaturated aldehydes is presented; the reaction provides access to 5-hydroxyisoxazolidines and beta-amino acids in high yields and with 90-99% ee.
Ibrahem
Ismail
I
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden.
Rios
Ramon
R
Vesely
Jan
J
Zhao
Gui-Ling
GL
Córdova
Armando
A
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
C518928:5-hydroxyisoxazolidine; D000447:Aldehydes; D000596:Amino Acids; D007202:Indicators and Reagents; D010080:Oxazoles