Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by L-tryptophan in the presence of water.
Primary amino acids and their derivatives were investigated as catalysts for the direct asymmetric aldol reactions between ketones and aldehydes in the presence of water, and L-tryptophan was shown to be the best catalyst. Solvent effects, substrate scope and the influence of water on the reactions were investigated. Quantum chemical calculations were performed to understand the origin of the observed stereoselectivity.
Jiang
Zhaoqin
Z
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Republic of Singapore.
Yang
Hui
H
Han
Xiao
X
Luo
Jie
J
Wong
Ming Wah
MW
Lu
Yixin
Y
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014364:Tryptophan / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D012997:Solvents; D014867:Water; D014364:Tryptophan