期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 13, 页码 4338-4341出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01375
关键词
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资金
- MEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University
- JSPS (KAKENHI) [15H03804, 15K13633, 14J02341]
- Grants-in-Aid for Scientific Research [14J02341, 15H03804] Funding Source: KAKEN
We have developed a novel approach for the synthesis of enantio enriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives. This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theoretical study of the reaction mechanism is also described.
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