Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.
Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
Jie
J
Guang
Qunsheng
Q
Guo
John Cong-Gui
JC
Zhao
D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D000081:Acetamides / Q000737:chemistry*; D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
D000081:Acetamides; D000085:Acetates; C003126:phosphonoacetaldehyde; C030686:acetamide; D000079:Acetaldehyde