SIMPLE SYNTHESIS OF L-VINYLGLYCINE AND D-VINYLGLYCINE (2-AMINOBUT-3-ENOIC ACID) AND RELATED AMINO-ACIDS
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 0300-922XFull text not available from this repository.
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|
|Official Date:||21 December 1994|
|Number of Pages:||7|
|Page Range:||pp. 3537-3543|
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