title: Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water.
abstract: A new series of water compatible primary-tertiary diamine catalysts derived from natural primary amino acids bearing a hydrophobic side chain have been synthesized. These new primary-tertiary diamine-Brønsted acid conjugates bifunctional organocatalysts efficiently catalyzes the asymmetric direct syn selective cross-aldol reaction of different protected hydroxyacetone with various aldehydes in high yield (94%) and high enantioselectivity (up to 97% ee of syn) and dr of 91 : 9 (syn/anti) under mild reaction conditions.
authors.affiliation: Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar-143005, India.
authors.forename: Akshay
authors.initials: A
authors.lastname: Kumar
authors.forename: Sarbjit
authors.initials: S
authors.lastname: Singh
authors.forename: Vikas
authors.initials: V
authors.lastname: Kumar
authors.forename: Swapandeep Singh
authors.initials: SS
authors.lastname: Chimni
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D014867:Water; D000096:Acetone; C004433:acetol; C116609:3-hydroxybutanal