Zinc(II)‐Catalyzed Intermolecular Hydrative Aldol Reactions of 2‐En‐1‐ynamides with Aldehydes and Water to form Branched Aldol Products Regio‐ and Stereoselectively |
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| Authors: | Dr. Appaso Mahadev Jadhav Dr. Vinayak Vishnu Pagar Dr. Deepak B. Huple Prof. Dr. Rai‐Shung Liu |
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| Affiliation: | Department of Chemistry, National Tsing‐Hua University, Hsinchu, 30043, Taiwan (ROC) |
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| Abstract: | This work describes zinc(II)‐catalyzed hydrative aldol reactions of 2‐en‐1‐ynamides with aldehydes and water to afford branched aldol products regio‐ and stereoselectively. The anti and syn selectivity can be modulated by the sizes of sulfonamides to yield E‐ and Z‐configured zinc(II) dienolates selectively. This new reaction leads to enantiopure aldol products by using a cheap chiral sulfonamide. The mechanistic analysis reveals that the sulfonamide amides of the substrates can trap a released proton to generate dual acidic sites to activate a carbonyl allylation reaction. |
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| Keywords: | aldol reaction stereoselectivity sulfonamides synthetic methods zinc |
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