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ChemInform Abstract: Studies on the Reaction of Dimethyl (2S,4RS)-N-Phthaloyl-4-bromoglutamate with Aldehydes and Ketones under Reformatsky Conditions.

✍ Scribed by A. N. GRISHAKOV; T. V. MATVEEVA; V. P. KRASNOV

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199837227

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✦ Synopsis

Studies on the Reaction of Dimethyl (2S,4RS)-N-Phthaloyl-4bromoglutamate with Aldehydes and Ketones under Reformatsky Conditions.

-The reaction of dimethyl N-phthaloyl-4-bromoglutamate (I) under Reformatsky conditions is studied. Reaction of compound (I) with aliphatic aldehydes and ketones under Reformatsky conditions proceeds as intramolecular cyclization with participation of the phthalimide carbonyl group to afford the pyrrolidinoisoindolinone (II), which undergoes dehydration in refluxing acetic anhydride. Reformatsky reaction of compound (I) with aromatic aldehydes (IV) provides the expected benzylideneglutaminic acid derivatives (V) in low yields. -(GRISHAKOV, A.

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