(S)-Proline-derived new chiral ligands with phosphino,organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating element |
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| Institution: | 1. School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China;2. Department of Chemistry, LanzhouUniversity, Lanzhou, Gansu, 730000, China;1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran;2. School of Chemistry, Physics and Earth Sciences, Flinders University, Adelaide 5001, Australia;1. Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049–001 Lisbon, Portugal;2. Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan;3. Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya Str., Moscow 117198, Russian Federation;4. Department of Ecology and Soil Sciences, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan;1. Fundação Oswaldo Cruz, Instituto Oswaldo Cruz, Laboratório de Bioquímica de Proteínas e Peptídeos, 21040-360, Rio de Janeiro, RJ, Brazil;2. Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, Campus do Valonguinho, 24210-141, Niterói, RJ, Brazil;3. Fundação Oswaldo Cruz, Instituto Oswaldo Cruz, Laboratório de Imunologia Clínica, 21040-360, Rio de Janeiro, RJ, Brazil;1. Department of Chemistry, Faculty of Science, Toho University, Funabashi, Chiba 274-8510, Japan;2. Research Center for Materials with Integrated Properties, Toho University, Funabashi, Chiba 274-8510, Japan;1. Reshetnev Siberian State University of Science and Technology, Krasnoyarsk 660049, Russia;2. Institute of Nanotechnology, Spectroscopy and Quantum Chemistry, Siberian Federal University, Krasnoyarsk 660041, Russia |
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| Abstract: | The synthesis of (S)-proline-derived chiral ligands bearing phosphino, organosulfur or selenenyl groups and their use as chiral ligands in palladium-catalyzed asymmetric allylic alkylations has been accomplished. In particular, the (S)-proline-derived phosphine ligands bearing alkylsulfenyl groups provided high enantioselectivity, and the degree of asymmetric induction was dependent upon the steric bulk of the alkyl substituents in sulfenyl groups. The stereochemical results are rationalized by a plausible mechanism involving the assistance of chelates formed by the participation of the two preferred heteroatoms involved. |
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