Asymmetric synthesis of bicyclic piperidines via L-proline catalyzed aldol reaction of 3-phthalimidopropanal |
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Authors: | Zhang Fanglin Peng Yiyuan Gong Yuefa |
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Affiliation: | Department of Chemistry, Huazhong University of Science and Technology, Hubei, China. |
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Abstract: | A highly enantioselective approach for preparing optically active bicyclic piperidines is described. The key step for introducing chiral centers was a L-proline catalyzed direct enantioselective aldol reaction of 3-phthalimidopropanal with aliphatic ketones. In the reactions with alicyclic ketones, a highly enantioselective formation of anti-2-(3-phthalimido-1-hydroxypropyl)cycloketones 1a-1b (>99% ee) was observed. The aldol products 1 could be subsequently converted into bicyclic piperidines 2 via a consecutive reductive deprotection, acylation, ring closure, and hydrolysis. |
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Keywords: | enantioselective bicyclic piperidines L‐proline 3‐phthalimidopropanal aldol reaction |
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