Deaminative and decarboxylative catalytic alkylation of amino acids with ketones
It cuts two ways: The cationic [Ru-H] complex catalyzes selective coupling of α- and β-amino acids with ketones to form α-alkylated ketone products. The reaction involves C-C and C-N bond cleavage which result in regio- and stereoselective alkylation using amino acids. A broad substrate scope and high functional-group tolerance is demonstrated. Copyright
Kalutharage, Nishantha,Yi, Chae S.
supporting information
p. 13651 - 13655
(2014/01/06)
Titanocene-catalyzed conjugate reduction of αβ-unsaturated carbonyl derivatives
"Chemical Equation Presented" A titanocene-catalyzed conjugate reduction of αβ-unsaturated carbonyl derivatives has been developed. A series of carbonyl compounds including aldehydes, ketones, esters, and amides proved viable in the reduction process providing an efficient, chemoselective method for the catalytic reduction of unsaturated carbonyl derivatives.
Ashfeld, Brandon L.,Kosal, Andrew D.
scheme or table
p. 44 - 47
(2010/03/03)
Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates. A comparative study with lithium enolates
Alkylation of regioisomeric potassium enolates 4 and 6 obtained from corresponding silyl enol ethers 2 and 3 occurs at the most substituted site affording ketones 8. Alkylation of corresponding lithium enolates 5 and 7 occurs at the expected site affording ketones 8 or 9. As an application the one pot synthesis of spiroketones 13 from silyl enol ethers 12 is described.
Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones
Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.
Kuwajima, Isao,Nakamura, Eiichi,Shimizu, Makoto
p. 1025 - 1030
(2007/10/02)
Alkylation via tris(dialkylamino)sulfonium enolates
Tris(dialkylamino)sulfonium enolates generated from tris(diethylamino)sulfonium difluorotrimethylsiliconate and enol silyl ethers are readily alkylated by various alkyl halides under mild conditions.
Noyori,Nishida,Sakata
p. 2085 - 2088
(2007/10/02)
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