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

Autor: Vadim A. Davankov, Alexei A. Shiryaev, O. V. Potapova, I. V. Chuchelkin, I. M. Novikov, Konstantin N. Gavrilov, E. A. Rastorguev, Pavel V. Petrovskii, Sergey V. Zheglov
Rok vydání: 2012
Předmět:
Zdroj: Russian Chemical Bulletin. 61:1925-1932
ISSN: 1573-9171
1066-5285
DOI: 10.1007/s11172-012-0267-3
Popis: 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.
Databáze: OpenAIRE