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• W2054967080 endingPage "1961" @default.
• W2054967080 startingPage "1957" @default.
• W2054967080 abstract "Enantiomerically pure vinylglycine (4b) can be prepared from natural („chiral pool”︁) amino acids by photoelimination of γ-functionalized N-phthaloyl amino acid esters. Two routes have been developed: (a) a three-step synthesis of substrate 3b [PhtN-Met(SO)OMe] from (S)-methionine and subsequent photolysis, (b) the use of N-phthaloyl activated methyl 2-amino-4-chloro- or -4-bromobutanoates 3d, e which are available from (S)-methionine (four-step synthesis) or from (S)-homoserine (two-step synthesis). The photoelimination (of HOSMe from 3b and of HX from 3d, e) proceeds quantitatively and leads to N,C-protected vinylglycine 4a in high yields. This strategy could also be applied to peptide-bound substrates as was shown for the protected Met-Gly (5b) which was transformed into the N-protected vinylglycine-glycine dipeptide 6 in three steps." @default.
• W2054967080 created "2016-06-24" @default.
• W2054967080 creator A5019289954 @default.
• W2054967080 creator A5039166426 @default.
• W2054967080 date "1995-11-01" @default.
• W2054967080 modified "2023-09-23" @default.
• W2054967080 title "A photochemical route to vinylglycine and a vinylglycine dipeptide" @default.
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• W2054967080 doi "https://doi.org/10.1002/jlac.1995199511275" @default.
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