Synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylate via silver/ThioClickFerrophos-catalyzed asymmetric 1,3-dipolar cycloaddition of dihydropyrrole ester with N-substituted maleimide |
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Authors: | Atsuo Tada Sayo WatanabeMidori Kimura Yuichiro TokoroShin-ichi Fukuzawa |
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Institution: | Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan |
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Abstract: | The AgOAc/ThioClickFerrophos-complex catalyzed the 1,3-dipolar cycloaddition of 3,4-dihydropyrrole-2-carboxylates, a precursor of cyclic azomethine ylides, with N-substituted maleimide to give the exo-cycloadducts, that is, 7-azabicyclo2.2.1]heptane-1-carboxylates, as the major product in moderate yields with a high enantiomeric excess (up to 86% ee) under the optimized conditions. Michael adducts were produced as a minor product. |
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Keywords: | Cycloaddition Azomethine ylide Silver Chiral ferrocene Dihydropyrrole |
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