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Synthesis of 3-Substituted 4-Piperidinones via a One-Pot Tandem Oxidation−Cyclization−Oxidation Process: Stereodivergent Reduction to 3,4-Disubstituted Piperidines

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NIAID Data Ecosystem2026-03-06 收录
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https://figshare.com/articles/dataset/Synthesis_of_3_Substituted_4_Piperidinones_via_a_One_Pot_Tandem_Oxidation_Cyclization_Oxidation_Process_Stereodivergent_Reduction_to_3_4_Disubstituted_Piperidines/3341101
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A novel approach to 3-substituted 4-piperidinones is described. The one-pot tandem oxidation−cyclization−oxidation of unsaturated alcohols 1a−e by PCC or PCC and trifluoromethanesulfonic acid affords piperidinones 2a−e in good yield. Reduction of 2a−e by L-Selectride gives the corresponding cis 3,4-disubstituted piperidines with diastereomeric ratios of >99:1. By contrast, reduction of 2a−e by Al-isopropoxydiisobutylalane gives the trans products with diastereomeric ratios of up to 99:1.
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2016-05-07
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