Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N
2,3-dimethyl-N
1-phenylpentane-1,2-diamine |
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| Authors: | K N Gavrilov I V Chuchelkin S V Zheglov A A Shiryaev O V Potapova I M Novikov E A Rastorguev P V Petrovskii V A Davankov |
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| Institution: | 1267. S. A. Esenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation
2267. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation
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| Abstract: | The synthesis of new P*-mono- and P*,N-bidentate diamidophosphites, containing 1,3,2-diazaphospholidine rings formed starting from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine, is described. Comparison of their efficiency in the Pd-catalyzed enantioselective allylation with (E)-1,3-diphenylallyl acetate showed that up to 97% ee was reached in the reaction involving dimethyl malonate as a C-nucleophile. The Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate gave up to 61% ee. |
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