Tetrahedron p. 1889 - 1897 (2000)
Update date:2022-07-29
Topics:
Black, David Stc.
Edwards, Gavin L.
Evans, Richard H.
Keller, Paul A.
Laaman, Sean M.
Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding γ-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. (C) 2000 Elsevier Science Ltd.
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