Aziridinylethers as highly enantioselective ligands for the asymmetric addition of organozinc species to carbonyl compounds

In the present paper a straightforward and efficient method for the synthesis of new chiral aziridinylether systems has been described. All of the new compounds have been tested in two stereocontrolled addition reactions of organozinc species to carbonyl compounds. The addition of diethyl- and phenylethynylzinc to aryl and alkyl aldehydes afforded the corresponding chiral products in high chemical yields (up to 90%) and with excellent ee’s of approximately 93%.

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(R)-(+)-2-Methyl-1-(2-phenoxyethyl)aziridineC11H15NOEe = 99%[α]D20 = +4.0 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R) (literature data)

(R)-(−)-1-(2-Phenoxyethyl)-2-(propan-2-yl)aziridineC13H19NOEe = 99%[α]D20 = −0.3 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R) (literature data)