Catalytic asymmetric allylation of 3,4-dihydroisoquinolines and its application to the synthesis of isoquinoline alkaloids
| Autor: | Hiromi Fukuoka, Takashi Itoh, Kazuhiro Nagata, Takuya Kanemitsu, Yuki Odanaka, Keita Sugai, Kazuo T. Nakamura, Yuki Seito, Nami Ando, Michiko Miyazaki |
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| Rok vydání: | 2010 |
| Předmět: |
Magnetic Resonance Spectroscopy
Molecular Structure Organic Chemistry Chiral ligand Enantioselective synthesis Stereoisomerism Isoquinolines Ligands Chemical synthesis Catalysis Adduct chemistry.chemical_compound Alkaloids Nucleophile chemistry Moiety Organic chemistry Stereoselectivity Organosilicon Compounds Isoquinoline Copper |
| Zdroj: | The Journal of organic chemistry. 76(2) |
| ISSN: | 1520-6904 |
| Popis: | A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A. |
| Databáze: | OpenAIRE |
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