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SIMPLE SYNTHESIS OF L-VINYLGLYCINE AND D-VINYLGLYCINE (2-AMINOBUT-3-ENOIC ACID) AND RELATED AMINO-ACIDS
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UNSPECIFIED (1994) SIMPLE SYNTHESIS OF L-VINYLGLYCINE AND D-VINYLGLYCINE (2-AMINOBUT-3-ENOIC ACID) AND RELATED AMINO-ACIDS. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (24). pp. 3537-3543. ISSN 0300-922X.
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Abstract
A three-step synthesis of vinylglycine 1 has been developed using a readily available starting material (but-3-enenitrile 2), based on the Neber rearrangement of the corresponding N-chloroimidate, and using cheap, convenient reagents. Also described is a convenient optical resolution of the N-tert-butoxycarbonyl derivative by papain-catalysed enantioselective esterification in a two-phase system. From the optically active amino acid, related amino acids obtained via epoxidation, dihydroxylation and cyclopropanation have been prepared. The related beta,gamma-unsaturated amino acids (E)-2-aminopent-3-enoic acid 20 and (E)-2-amino-3-methylpent-3-enoic acid 22 have been synthesised using the same approach.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | ||||
Publisher: | ROYAL SOC CHEMISTRY | ||||
ISSN: | 0300-922X | ||||
Official Date: | 21 December 1994 | ||||
Dates: |
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Number: | 24 | ||||
Number of Pages: | 7 | ||||
Page Range: | pp. 3537-3543 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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