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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.

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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
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:
DateEvent
21 December 1994UNSPECIFIED
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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