Palladium(0) catalyzed enantioselective rearrangement of O-allylic thiocarbamates to S-allylic thiocarbamates: asymmetric synthesis of allylic thiols |
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| Affiliation: | 1. Department of Chemistry, Osmania University, Hyderabad, Telangana State 500004, India;2. Organic Catalysis and Biocatalysis Laboratory OCBL/FACET, Federal University of Grande Dourados—UFGD, Dourados/Itahúm rod. km 12 s/n, Zip Code 79804-970, Dourados, MS, Brazil;1. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Campus Universitario, E-28871 Alcalá de Henares, Spain;2. Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Spain;3. Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, Campus Universitario, E-28871 Alcalá de Henares, Spain;1. Lab of Plant Development, Shanghai Key Laboratory of Bio-Energy Crops, Plant Science Center, School of Life Sciences, Shanghai University, Shanghai, 200444, China;2. School of Environmental and Chemical Engineering, Shanghai University, Shanghai, 200444, China;1. School of Environmental and Chemical Engineering, Shanghai University, Shanghai, 200444, China;2. School of Life Sciences, Shanghai University, Shanghai, 200444, China;3. Shanghai Xuhui Center Hospital, Shanghai, 200031, China;4. School of Science and Engineering, Saitama University, Saitama, 338-8570, Japan |
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| Abstract: | The Pd(0) catalyzed rearrangement of the O-allylic thiocarbamates rac-2a, rac-2b and rac-4 in the presence of the chiral bisphosphane 5 proceeded quantitatively and gave the S-allylic thiocarbamates 6a, 6b and 7, respectively, with 91, 92 and 97% ee, respectively, in high yields. Saponification of the S-allylic thiocarbamate 7 furnished the allylic thiol 9 with 97% ee. |
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