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|Title:||Solid-phase synthesis of β-keto esters via sequential baylis - Hillman and heck reactions|
|Authors:||Kulkarni, B.A. |
|Citation:||Kulkarni, B.A.,Ganesan, A. (1999). Solid-phase synthesis of β-keto esters via sequential baylis - Hillman and heck reactions. Journal of Combinatorial Chemistry 1 (5) : 373-378. ScholarBank@NUS Repository.|
|Abstract:||Acrylic acid was immobilized on polystyrene - Wang resin, followed by Baylis - Hillman reaction with aldehydes using DABCO as catalyst. Addition of 1 equiv of lanthanum(III) trifluoromethanesulfonate was found to improve yields, as in solution phase. After the Baylis - Hillman step, Heck reaction with aryl halides resulted in α-substituted β-keto esters, which were cleaved from the resin by acid hydrolysis with concomitant decarboxylation to afford aryl ketone products. Overall yields of 0-49% were obtained with 26 examples.|
|Source Title:||Journal of Combinatorial Chemistry|
|Appears in Collections:||Staff Publications|
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