title: Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols.
abstract: An efficient direct asymmetric aldol reaction between hydroxyacetone and β,γ-unsaturated α-keto esters has been successfully developed. In the presence of 9-amino-9-deoxy-epi-cinchonine and trifluoroacetic acid, the direct aldol reaction of O-protected hydroxyacetone proceeded in a highly enantioselective manner, affording the desired adducts containing a chiral tertiary alcohol in high yields and with excellent enantioselectivities. The aldol products obtained are valuable precursors for the synthesis of 2-substituted glycerol derivatives.
authors: Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.
authors: Chen
authors: C
authors: Liu
authors: Xiaowei
authors: X
authors: Dou
authors: Yixin
authors: Y
authors: Lu
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004952:Esters; D000096:Acetone; C004433:acetol