Asymmetric synthesis of amino acids via the catalytic reduction of acylaminoacrylic acid azlactone derivatives 24. Reductive aminolysis of 2-methyl-4-benzylidene-Δ2-oxazolin-5-one upon treatment with a catalytic system based on S-phenylalanine derivatives Full article
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Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230 |
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Output data | Year: 1990, Volume: 39, Number: 4, Pages: 720-726 Pages count : 7 DOI: 10.1007/bf00960334 | ||
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Abstract:
Reductive aminolysis of 2-methyl-4-benzylidene-Δ2-oxazolin-5-one upon treatment with a PdCl2-S-phenylalanine ester (dimethylamide) catalytic system leads to the formation of the corresponding acylated dipeptide derivatives, with the R,S-configuration (diastereomer) predominating (DE 9–27%). The reaction stereoselectivity in dimethoxyethane increases sharply in the presence of triethylamine additive, and in the case of S-phenylalanine methyl ester reaches 47%. The stepwise mechanism for this process has been studied.
Cite:
Lyubeznova M.R.
, Karpeiskaya E.I.
, Klabunovskii E.I.
Asymmetric synthesis of amino acids via the catalytic reduction of acylaminoacrylic acid azlactone derivatives 24. Reductive aminolysis of 2-methyl-4-benzylidene-Δ2-oxazolin-5-one upon treatment with a catalytic system based on S-phenylalanine derivatives
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1990. V.39. N4. P.720-726. DOI: 10.1007/bf00960334 OpenAlex
Asymmetric synthesis of amino acids via the catalytic reduction of acylaminoacrylic acid azlactone derivatives 24. Reductive aminolysis of 2-methyl-4-benzylidene-Δ2-oxazolin-5-one upon treatment with a catalytic system based on S-phenylalanine derivatives
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1990. V.39. N4. P.720-726. DOI: 10.1007/bf00960334 OpenAlex
Identifiers:
OpenAlex: | W3011444632 |
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