Stereoselective Formal Hydroamidation of Si-Substituted Arylacetylenes with DIBAL-H and Isocyanates: Synthesis of (E)- and (Z)-α-Silyl-α,β-unsaturated Amides
Hanseul Lee, Soohong Cho, Yunmi Lee* and Byunghyuck Jung*
*Kwangwoon University, Seoul 01897; Daegu Gyeongbuk Institute of Science and Technology, Daegu 42988, Republic of Korea, Email: ymleekw.ac.kr, byunghyuck.jungdgist.ac.kr
H. Lee, S. Cho, Y. Lee, B. Jung, J. Org. Chem., 2020, 85, 12024-12035.
DOI: 10.1021/acs.joc.0c01903 (free Supporting Information)
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Solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that react with isocyanates at ambient temperature to afford α-silyl-α,β-unsaturated amides in high yields. This method offers short reaction time, ease of purification, easily accessible substrates, and gram-scale synthesis.
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