Diborylalkyllithium Salts Trigger Regioselective Ring Opening of Vinyl Aziridines

Identifier:  imarina:6003798

Handle: https://hdl.handle.net/20.500.11797/imarina6003798

Authors:  Salvado, Oriol; Gava, Riccardo; Fernandez, Elena

Abstract:
gem-Diborylalkanes treated with LiTMP produce alpha-diborylalkane lithium bases that perform nucleophilic attack on vinyl aziridines with controlled regioselectivity. Preferred S(N)2 diborylalkylation ring opening reaction on the less sterically hindered position is observed with 1-tosyl-2-vinylaziridine, whereas exclusive S(N)2' nucleophilic attack occurs on 2-methyl-1-tosyl-2-vinylaziridine. Cyclic vinyl aziridines interact through a third venue, via S(N)2 diborylalkylation ring opening reaction on the allylic position. Homoallylic diboronates are formed with complete stereochemical control.