Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system.
The direct three-component Mannich reactions of O-benzyl hydroxyacetone with p-anisidine and aromatic or aliphatic aldehydes in the presence of an L-threonine-derived catalyst afforded anti-1,2-amino alcohols in good-to-excellent yields and with enantioselectivities of up to 97%. This study is the first demonstration that direct three-component Mannich reactions can be promoted by a primary amino acid in water.
Cheng
Lili
L
Department of Chemistry, National University of Singapore, Republic of Singapore. chmlyx@nus.edu.sg
Wu
Xiaoyu
X
Lu
Yixin
Y
D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013912:Threonine / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D000605:Amino Alcohols; D000814:Aniline Compounds; D001555:Benzene Derivatives; D014867:Water; D013912:Threonine; C013813:4-anisidine