103754-42-3Relevant academic research and scientific papers
Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
Meier, Lidiane,Ferreira, Misael,Sa, Marcus M.
, p. 179 - 186 (2012/07/14)
A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.
A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis-Hillman adducts and a simple access to some important insect pheromones
Das, Biswanath,Chowdhury, Nikhil,Banerjee, Joydeep,Majhi, Anjoy
, p. 6615 - 6618 (2007/10/03)
An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, with Al-NiCl2·6H2O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone.
Synthetic applications of Baylis-Hillman chemistry: An efficient and solely stereoselective synthesis of (E)-α-methylcinnamic acids and potent hypolipidemic agent LK-903 from unmodified Baylis-Hillman adducts
Das, Biswanath,Banerjee, Joydeep,Chowdhury, Nikhil,Majhi, Anjoy
, p. 1725 - 1727 (2007/10/03)
An efficient and solely stereoselective synthesis of (E)-α- methylcinnamic acids has been accomplished in single pot by reduction of the unmodified Baylis-Hillman adducts, methyl-3-hydroxy-3-aryl-2- methylenepropanoates with I2/NaBH4 reagent system at room temperature followed by hydrolysis. The efficacy of this method has been proved in the total synthesis of 1-[p-(myristyloxy)-α-methylcinnamoyl]glycerol, LK-903, a highly active hypolipidemic agent.
A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids
Basavaiah,Krishnamacharyulu,Hyma,Sarma,Kumaragurubaran
, p. 1197 - 1200 (2007/10/03)
A simple and convenient stereoselective synthesis of [E]-α- methylcinnamic acids via the nucleophilic addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates followed by hydrolysis and crystallization is described
