Frolov A. Selective introduction of an alkyl substituent into α­-position of carbonyl compounds.

The thesis is devoted to elaboration of α-­alkylation methods of carbonyl compounds. Major synthetic results include synthesis of enaminones at amounts of 100­200 g with their following modification via interaction with organometallic reagents and/or catalytic hydrogenation. A scalable, concise, relatively simple, safe and economically reasonable synthetic sequence for introduction of methyl, primary alkyl and secondary alkyl groups into α­position of diverse carbonyl compounds. Optimal conditions for each step were designed after analysis of model experiment results as well as existing literature methods of enaminone synthesis and modification. After the optimization stage, the chosen conditions were applied to the representative array of substrates, mainly non­aromatic endocyclic ketones that are investigated in Part 2 and Part 3. Scope and limitations of the method were explored. Both positive and negative results were explained. In case of unclear stereochemistry, configuration of the products was determined by either X­rays diffraction or 2D ЯМР experiments.