Development of P1-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations |
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Authors: | Konstantin N Gavrilov Alexei A Shiryaev Sergey V Zheglov Oksana V Potapova Ilya V Chuchelkin Ivan M Novikov Eugenie A Rastorguev Vadim A Davankov |
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Institution: | 1. Department of Chemistry, Ryazan State University, 46 Svoboda Street, 390000 Ryazan, Russian Federation;2. Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation |
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Abstract: | We have designed and synthesized a small library of modular monodentate diamidophosphite ligands with stereogenic phosphorus atoms. The library was prepared efficiently from the commercially available and inexpensive (S)-N-Boc-amino acids. These novel ligands were screened in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate with dimethyl malonate as the C-nucleophile with up to 93% ee being obtained. The results showed that the different substituents in the 1,3,2-diazaphospholidine cycle had remarkable effects on the enantioselectivity. |
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