Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group |
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| Authors: | Duanshuai Tian Dr Chengxi Li Dr Guoxian Gu Henian Peng Prof Dr Xumu Zhang Prof Dr Wenjun Tang |
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| Institution: | 1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, P. R. China;2. Department of Chemistry, South University of Science and Technology of China, Shenzhen, P. R. China |
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| Abstract: | Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition‐metal‐free coupling between chiral α‐aryl‐α‐mesylated acetamides and arylboronic acids provided access to a series of chiral α,α‐diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB1 receptor ligand, the antidepressant (S)‐diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method. |
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| Keywords: | arylboronic acids enantioselectivity nucleophilic substitution stereospecificity α α -diaryl acetamides |
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