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Diamidophosphites with isomeric carborane fragments: a comparison of catalytic activity in asymmetric Pd-catalyzed allylic substitution reactions |
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| Authors: | Sergey E. Lyubimov Vadim A. Davankov Tatiana B. Grishina Andrey A. Tyutyunov Valery N. Kalinin |
| Affiliation: | a Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation b Department of Chemistry, Ryazan State University, 46 Svoboda Street, 390000 Ryazan, Russian Federation c Institut für Anorganische Chemie, Johannisallee 29, 04103 Leipzig, Germany |
| Abstract: | New chiral diamidophosphite ligands containing electron-donating 9-meta-carborane and electron-withdrawing 1-meta-carborane substituents have been synthesized. The ligand 3a with an electron-donating group demonstrated high enantioselectivity in Pd-catalyzed allylic substitution reactions with C-, S- and N-nucleophiles (up to 98% ee). The isomeric diamidophosphite 3b bearing an electron-withdrawing substituent showed in all cases, moderate-to-poor conversion and lower enantioselectivity. |
| Keywords: | Asymmetric allylic alkylation Palladium Carboranyldiamidophosphites Electronic effect |
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