Michael Addition Methyl Vinyl Ketone And

Propargylamines are synthesized from methyl vinyl ketone derivatives 1 alkynes and secondary amines catalyzed by cu salts involving the michael addition of amine followed by an unusual c c bond cleavage and addition of metal acetylides formed in situ to iminium ions.

Michael addition methyl vinyl ketone and.

The michael addition and the aldol condensation. The michael reaction or michael addition is the nucleophilic addition of a carbanion or another nucleophile to an α β unsaturated carbonyl compound containing an electron withdrawing group it belongs to the larger class of conjugate additions this is one of the most useful methods for the mild formation of c c bonds. The carbonyl containing compound is attacked by the base in the first step of the michael addition mechanism. Michael addition reaction can also be carried out with alkali metals like cs in zeolite and mesoporous molecular sieve catalyst prepared by cationic exchange method giving 96 enantioselectivity of product by using raw materials such as methyl vinyl ketone and malononitrile but these catalysts only provide high basicity which is useful for.

Addition to acrylonitrile of 1 yielded α n a dicyanoethyltryptophan methyl ester 3. The method uses a ketone and a methyl vinyl ketone to form an α β unsaturated ketone in a cyclohexane ring by a michael addition followed by an aldol condensation. Michael addition mechanism step 1. Diethyl malonate with methyl crotonate.

The reactions could be carried out without any catalysts and solvents. The reaction donors are active methylenes such as malonates and nitroalkanes and the acceptors are activated olefins such as α β unsaturated carbonyl compounds. Silica gel mediated michael addition of 1 3 dicarbonyl compounds to methyl vinyl ketone mvk and ethyl vinyl ketone evk was carried out to give the corresponding adducts in quite excellent yields. The first step in the process is the michael addition to an α β unsaturated ketone such as methyl vinyl ketone ethyl vinyl ketone is shown above.

Michael addition to methyl acrylate and methyl vinyl ketone of n b benzylidene l tryptophan methyl ester 1 gave 2 3 indolylmethyl glutamic dimethyl ester 2a and α 3 oxobutyl tryptophan methyl ester 2b respectively. It was discovered by robert robinson in 1935 as a method to create a six membered ring by forming three new carbon carbon bonds. In this approach the di tri and tetrasubstituted propargylamines are synthesized in 46 98 yields. 2 nitropropane with methyl acrylate.

Mechanism of the robinson annulation. The michael addition is thermodynamically controlled. Mesityl oxide with diethyl malonate. In this scheme r and r on the.

Hydrolysis of ester groups and decarboxylation occurs in the final step. The 1 4 addition or conjugate addition of resonance stabilized carbanions. It combines two reactions. Diethyl malonate with diethyl fumarate.

The robinson annulation is a chemical reaction used in organic chemistry for ring formation. 1 michael addition of diethyl malonate with methyl vinyl ketone followed by protic workup yields a 1 5 dicarbonyl compound.