4629-80-5Relevant articles and documents
Selective α-Methylation of Ketones
Frolov, Andriy I.,Ostapchuk, Eugeniy N.,Pashenko, Alexander E.,Chuchvera, Yaroslav O.,Rusanov, Eduard B.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.
, p. 7333 - 7346 (2021/06/28)
The convenient and scalable preparative approach for the two-step α-methylation of ketones is described. The optimized protocols for regioselective preparation of enaminones with further diastereoselective and functional groups tolerant hydrogenation to α-methylketones are developed. The scope and limitations of the proposed methodology are discussed. The advantages compared to known procedures are demonstrated. The unexpected role of acetone in the hydrogenation is suggested. The evaluation of the method for both early building block synthesis and late-stage CH-functionalization is shown. The elaborate procedures' preparability and scalability are demonstrated by the synthesis of several α-methyl ketones up to 100 g amount.
DETERMINATION OF THE CONFIGURATIONS OF ALCOHOLS AND ISOCYANATES BY KINETIC RESOLUTION
Potapov, V. M.,Gracheva, R. A.,Okulova, V. F.
, p. 311 - 316 (2007/10/02)
The kinetic resolution of α-phenylethyl isocyanate was achieved by means of R-α-phenylethylamine, and S-α-benzylethylamine, S-salsolidine.The absolute configuration of α-phenylisobutyl isocyanate was determined on the basis of the relationship discoverd during the kinetic resolution of the isocyanate with these amines.The configurations of the carbon atom carrying the hydroxyl group in the cis and trans isomer of 1,3-dimethyl-4-piperidol were determined as a result of investigation of the stereochemical relationships in the reaction of α-phenyl-ethyl isocyanatewith alicyclic alcohols.A new asymmetric catalyst (S-N-methyl-salsolidine) is proposed for the kinetic resolution of alkylphenylcarbinols with α-phenylethyl isocyanate.