Thermolysis of dimethyl <Emphasis Type="Italic">cis</Emphasis>- and <Emphasis Type="Italic">trans</Emphasis>-1 pthalimidoaziridine-2,3-dicarboxylates in the presence of dipolarophiles |
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Authors: | M A Kuznetsov A V Ushkov S I Selivanov A S Pan’kova A Linden |
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Institution: | (1) Discovery Chemistry, Roche Research Center, Nutley, NJ 07110, USA;; |
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Abstract: | Thermolysis of dimethyl esters of stereoisomeric phthalimidoaziridine-2,3-dicarboxylic acids in the presence of dimethyl fumarate,
dimethyl maleate, and N-phenylmaleimide occurred stereo-specifically and stereoselectively led to the formation of derivatives of 1-phthalimidopyrrolidine,
products of 1,3-dipolar additrion of intermediately arising azomethine ylides. In keeping with the rules of the conservation
of orbital symmetry the thermal opening of the 2,3-disubstituted 1-phthalimidoaziridines into azomethine ylides occurred conrotatory.
The relative positions of the substituents in the dipolarophiles is retained in the reaction products indicating the concerted
addition mechanism. |
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