期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 19, 页码 12024-12035出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01903
关键词
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资金
- Basic Science Research Program through the National Research Foundation of Korea (NRF) [2020R1G1A1004460, 2020R1A2C1005817]
- Kwangwoon University
- National Research Foundation of Korea [2020R1A2C1005817, 2020R1G1A1004460] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
An efficient and stereoselective method for the synthesis of (E)- and (Z)-alpha-silyl-alpha,beta-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford alpha-silyl-alpha,beta-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-alpha-silyl-alpha,beta-unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds.
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