Palladium‐Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles |
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| Authors: | Dr Jianyou Mao Dr Jiadi Zhang Hui Jiang Dr Ana Bellomo Mengnan Zhang Zidong Gao Dr Spencer D Dreher Prof Patrick J Walsh |
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| Institution: | 1. Department of Applied Chemistry, China Agricultural University, Beijing, P. R. China;2. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA;3. Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ, USA;4. http://titanium.chem.upenn.edu/walsh/ |
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| Abstract: | The first two highly enantioselective palladium‐catalyzed allylic alkylations with benzylic nucleophiles, activated with Cr(CO)3, have been developed. These methods enable the enantioselective synthesis of α‐2‐propenyl benzyl motifs, which are important scaffolds in natural products and pharmaceuticals. A variety of cyclic and acyclic allylic carbonates are competent electrophilic partners furnishing the products in excellent enantioselectivity (up to 99 % ee and 92 % yield). This approach was employed to prepare a nonsteroidal anti‐inflammatory drug analogue. |
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| Keywords: | allylic compounds arenes chromium enantioselectivity palladium |
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