Facile synthesis of alpha-substituted acrylate esters.
Treatment of 5-monosubstituted Meldrum's acids with dimethylmethyleneimmonium iodide (Eschenmoser's iodide salt) in methanol gives alpha-substituted acrylate methyl esters in good yields. Easy access to 5-monosubstituted Meldrum's acids allowed us to synthesize a wide variety of alpha-substituted acrylate methyl esters. The reaction conditions are mild and tolerate many functional groups commonly used in organic synthesis; thus, this new method has potential as an alternative to conventional preparative methods for alpha-substituted acrylate esters.
Hin
Bunda
B
Guilford Pharmaceuticals, Inc., 6611 Tributary Street, Baltimore, Maryland 21224, USA.
Majer
Pavel
P
Tsukamoto
Takashi
T
D000179:Acrylates / Q000138:chemical synthesis*; D002264:Carboxylic Acids; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D004952:Esters / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008666:Metalloendopeptidases / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
D000179:Acrylates; D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D004952:Esters; D007202:Indicators and Reagents; D008666:Metalloendopeptidases