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Title: | Synthesis of (E)-3-alkylidenepyrrolidines by nucleophilic ring closure of (E)-2-alkylidene-1,4-diol derivatives |
Authors: | Ballini, Roberto Bosica, Giovanna Mase, Aldo Petrini, Marino |
Keywords: | Carbonyl compounds Asymmetric synthesis |
Issue Date: | 2000 |
Publisher: | WILEY-VCH Verlag |
Citation: | Ballini, R., Bosica, G., Mase, A., & Petrini, M. (2000). Synthesis of (E)-3-alkylidenepyrrolidines by nucleophilic ring closure of (E)-2-alkylidene-1,4-diol derivatives. European Journal of Organic Chemistry, 2000, 16, 2927-2931. |
Abstract: | The synthesis of N-protected (E)-3-alkylidenepyrrolidines is reported. Nitroalkanes react with unsaturated 1,4-diesters and 1,4-keto esters, giving a tandem Michael addition/elimination of nitrous acid. The obtained 1,4-dicarbonyl compounds are reduced to the corresponding diols and then converted into their mesylates. Reaction of mesylates with benzylamine or 4-methylbenzenesulfonylamide affords the unsaturated pyrrolidines. Use of the sulfonylamide for the cyclization step has advantages over that of benzylamine, since it gives better yields of pyrrolidines, and furthermore, the benzenesulfonyl group can be efficiently removed in the presence of unsaturated bonds. |
URI: | https://www.um.edu.mt/library/oar//handle/123456789/24644 |
Appears in Collections: | Scholarly Works - FacSciChe |
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