Asymmetric Decarboxylative 1,4‐Addition of Malonic Acid Half Thioesters to Vinyl Sulfones: Highly Enantioselective Synthesis of 3‐Monofluoromethyl‐3‐Arylpropanoic Esters |
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| Authors: | Baokun Qiao Qian Liu Dr Hongjun Liu Dr Lin Yan Prof Zhiyong Jiang |
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| Institution: | 1. Institute of Chemical Biology, Henan University, Kaifeng, Henan, 475004 (P. R. China), Fax: (+86)?378‐2864‐665;2. Key Laboratory of Natural Medicine and Immuno‐Engineering of Henan Province, Henan University, Kaifeng, Henan, 475004 (P. R. China) |
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| Abstract: | An asymmetric decarboxylative 1,4‐addition of malonic acid half thioesters (MAHTs) to 2‐aryl‐substituted vinyl sulfones has been developed, yielding adducts with excellent enantioselectivity (up to 97 % ee). In view of tuning pKa values, a quinine‐based benzyl‐substituted thiourea was designed and demonstrated as the most efficient catalyst. The enantioselective synthesis of 3‐monofluorinated analogues of 3‐methyl indanone and (+)‐turmerone has been accomplished from decarboxylative 1,4‐addition adducts with satisfactory results. |
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| Keywords: | asymmetric synthesis decarboxylative 1 4‐addition monofluoromethylation organocatalysis vinyl sulfones |
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