Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A
| Autor: | Pei Fen Chiang, Ping Yu Wu, Hsyueh Liang Wu, Ting Shen Kuo, Wei Sian Li, Jia Hong Jian |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Aldimine 010405 organic chemistry Potassium Organic Chemistry Enantioselective synthesis Diastereomer chemistry.chemical_element Total synthesis 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Tosyl chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 20(1) |
| ISSN: | 1523-7052 |
| Popis: | The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (−)-crispine A. |
| Databáze: | OpenAIRE |
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