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Synteza i redukcja prochiralnych imin

Berniak T. A.

Wiadomości Chemiczne

2016

[Z] 70, 5-6

353--368

Natural chemical compounds and their derivatives could be used for designing new classes of anticancer, antifungal or antiviral drugs. One of those compounds is gossypol, isolated from grains of wool. Gossypol’s derivatives can freely penetrate the blood-brain barrier (BBB). This basic review considers synthesis and reduction of prochiral imines. Gossypol derivatives belong to imines. Imines as unstable compounds, hydrolyze in contact with a small amount of water. There are substrates for preparation of oximes and its derivatives. In this article three methods of imines production are presented. There are: (a) reaction of aldehyde or ketones with primary amine, (b) addition of Grignard reagents to nitriles and (c) pyrolysis of alkyl azide. The first one is discussed in details with specific description of the mechanism of both steps: first stage - addition to form a hemiaminal, second one – dehydration with formation of imine. Many conditions such as acid power, value of pH reaction and environment (preferably anhydrous) have influence on the formation rate of imines and determine each of two stages, i.e. addition and dehydration. Furthermore, the imines-enamines tautomeric and stereochemical aspects with possible attack of nucleophile molecules to the carbon atom of the C=N bond from the Si or Re side of prochiral imines as well as potential ways of imines reductions to amines by using commonly used reducers (NaCNBH3) are discussed. Moreover, two new methods of reduction are presented: the first – with using trichlor acids catalyzed chiral Lewis’s bases and the second one – asymmetric hydrogenation of imines.