Chemical and Pharmaceutical Bulletin p. 1927 - 1930 (1994)
Update date:2022-09-26
Topics:
Itaya
Shimizu
Nakagawa
Morisue
Vinylglycine (2) has been shown to undergo racemization under acidic conditions. Optically pure 2 was obtained from 2 · HCl by enzymatic hydrolysis through N-acetylvinylglycine (5), followed by recrystallization. (S)N-(Methoxycarbonyl)vinylglycine (6) was configurationally so unstable under acidic conditions that 6 could not be obtained from 2 in an optically pure form. On the other hand, configurationally stable (S)-N-(9-phenylfluoren-9-yl)vinylglycine methyl ester (9) was synthesized from (S)-homoserine; 9 was hydrolyzed with sodium hydroxide to afford the carboxylic acid 10 of more than 99% ee.
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Doi:10.1039/DT9950002763
(1995)Doi:10.1007/BF01165705
(1994)Doi:10.1002/prac.19933350508
(1993)Doi:10.1016/0223-5234(96)88251-1
(1995)Doi:10.1016/0040-4020(95)00374-H
(1995)Doi:10.1021/jo00905a037
(1975)
