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Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

✍ Scribed by David StC. Black; Gavin L. Edwards; Richard H. Evans; Paul A. Keller; Sean M. Laaman

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 151 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00094-6

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✦ Synopsis

Some C5 mono-and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding g-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement.

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