Jaunu metožu izveide aminospirtu sintēzei un C–H funkcionalizēšanai. New Methods for the Synthesis and C–H Functionalization of Amino Alcohols
Summary of the Doctoral Thesis
Jekaterina Boļšakova, Riga Technical University, Latvia
Alkynylglycinols A have found application as important multifunctional building blocks for the construction of complex molecules. Amino alcohol is a substructure of many pharmaceutically relevant compounds, therefore functionalization of amino alcohols is of high importance. C–H functionalization is a very attractive approach as it does not require pre-functionalized starting materials and stoichiometric amount of transition metal catalyst in contrast to traditionally used methods.
The aim of the Thesis is to develop new synthetic methods for the synthesis of ethynylglycinols and investigate C–H functionalization of phenylglycinols using cobalt catalysis.
As the result of Thesis, several new methods for the synthesis of ethynylglycinol derivatives were developed: 1) propargylic substitution of bis-imidates was successfully applied for the synthesis of racemic and enantioenriched ethynylglycinols; 2) Ritter reaction of ethynylglycol cobalt complexes was applied for the synthesis of quaternary ethynylglycinols; 3) new conditions for the decomplexation of alkyne-cobalt complexes were established using DDQ as an oxidant; 4) a new method for cobalt catalyzed C–H functionalization of phenylglycinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary was demonstrated. This constitutes efficient and regioselective synthesis method of enantioenriched dihydroisoquinoline derivatives.
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