Kleban I. Heteroaliphatic endo- and exo-cyclic vinylboronates

The dissertation is devoted to the development of convenient synthetic approaches to heteroaliphatic derivatives of exo- and endo-cyclic vinylboronic acids and their cyclopropanation with subsequent involvement in the Suzuki-Miyauri reaction is investigated. New approaches to the synthesis of heteroaliphatic derivatives of endo- and exo-cyclic vinylboronic acids was developed, which allows obtaining a series of oxygen-, sulfur- and nitrogen-containing vinylboropinacolates with different ring size, including enantiomerically pure vinylboropinacolates with an α-amino acid fragment in high yields. It was found that various derivatives of cyclopropaneboronic acids with different substituents in the ring can be obtained by means of the borodecarboxylation reaction. The stereochemistry of borodecarboxylation of cyclopropanoic acids was investigated and it was shown that only trans- isomers are formed in this reaction. The reactivity of heteroaliphatic endo- and exo-cyclic vinylboropinacolates in the reaction of cyclopropanation with diazomethane was studied, which allows obtaining bicyclic saturated derivatives of corresponding boronic acids.