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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.
Research output not available from this repository, contact author.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 | ||||
|---|---|---|---|---|---|
| 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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