Control of Six Contiguous Stereocenters in an Asymmetric Organocatalytic One‐Pot Michael/Michael/Aldol Addition Sequence |
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Authors: | Dieter Enders,Gregor Urbanietz,Elisa Cassens‐Sasse,Sebastian Keeß ,Gerhard Raabe |
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Abstract: | The asymmetric organocatalytic one‐pot synthesis of polyfunctionalized cyclohexanes is described. Starting from β‐keto esters, nitroalkenes and α,β‐unstaturated aldehydes and employing a bifunctional norephedrine‐based thiourea catalyst, six contiguous stereocenters including one quarternary center are generated. The one‐pot protocol follows a Michael/Michael/aldol addition sequence and affords the highly substituted cyclohexanes in moderate to very good yields (22–70%), diastereomeric ratios of dr>95:5 and excellent enantioselectivities of 91–99% ee. |
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Keywords: | asymmetric synthesis cyclohexanes one‐pot reaction organocatalysis thioureas |
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