FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing enantiomeric excess of asymmetrically alkynylated α-aminoesters of formula (III) in which R1 and R2 independently denote C1-7-alkyl, optionally substituted with phenyl or trimethylsilyl, or C3-5-cycloalkyl; Y denotes H or a nitrogen atom protecting group. The method involves reaction of α-iminoester of formula
(I), in which R1 and Y assume values given for formula III, with an alkyl containing a terminal triple bond, of formula
(II), in which R2 assumes values given for formula III, in the presence of a catalyst. The catalyst used contains a transition metal complex CuPF6·4MeCN or CuOTf·0.5C6H6 and a chiral ligand selected from
, enantiomers thereof and mixture of enantiomers thereof.
EFFECT: method provides high output of asymmetrically alkynylated α-aminoesters of formula (III), which can be used in synthesis as optically active derivatives of amino acids which do not occur naturally.
3 cl, 3 tbl, 4 ex
Authors
Dates
2011-11-27—Published
2006-05-17—Filed