Radchenko D. Conformationally constrained and achiral analogues of natural amino acids

The thesis is devoted to the synthesis of conformationally constrained and achiral analogues of natural amino acids. For the first time spiro[3.3]heptane skeleton was applied for designing of natural amino acids analogues (Glu, Asp), while 2-azaspiro[3.3]heptane one - for basic natural amino acids and y-aminobutyric acid. Glutamic acid analogues were obtained in optical active form; thus, two compounds were added to the library of chiral compounds with axial chirality. New method of synthesis for 2,6-disubstituted spiro[3.3]heptane derivatives were proposed using 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid as starting material. For the first time one-pot tandem Streker synthesis - nucleofilic substitution reaction was applied to d-functionalized ketones. Conditions of the reaction were optimized thus leading to improved yields of corresponding 2-cyanopiperidines.