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

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Abstract

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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Key Words

carboxylation, vinylsilanes, DIBAL-H

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ID: J42-Y2020