In:
European Journal of Organic Chemistry, Wiley, Vol. 2004, No. 13 ( 2004-07), p. 2833-2839
Abstract:
α‐Amino acid phenylhydrazides 1 readily react with levulinic acid to produce the imidazolidin‐4‐one intermediates 4 , which undergo a second ring closure to afford the dihydro‐1 H ‐pyrrolo[1,2‐ a ]imidazole‐2,5‐dione derivatives 5 . It has been established that the solvent polarity has a great influence on the rate of the second condensation reaction, but not on the first. A mechanism, supported by experimental evidence, has been proposed to explain how the imidazolidin‐4‐one intermediates 4 , obtained as expected as a mixture of two diastereoisomers, give a single isomer for the bicyclic derivatives 5 ; the absolute stereochemistry of these compounds has been determined by X‐ray crystallographic analysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2004:13
DOI:
10.1002/ejoc.200400112
Language:
English
Publisher:
Wiley
Publication Date:
2004
detail.hit.zdb_id:
1475010-7
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