Photoinduced multicomponent synthesis of α-silyloxy acrylamides, an unexplored class of silyl enol ethers

Journal article

The photoinduced, multicomponent reaction of α-diazoketones, silanols, and isocyanides affords α-silyloxy acrylamides, formally derived from α-keto amides. The presence of a secondary amido group makes classic preparative methods for silyl enol ethers unfeasible in this case, while the mild conditions required by this photochemical approach allow their synthesis in good yields; moreover, the general structure can be easily modified by varying each component of the multicomponent reaction. Fine-tuning of the reaction conditions (i.e., solvents, radiation, additives) can be exploited to obtain complete Z selectivity. The reactivity of this overlooked class of silyl enol ethers has been investigated, and features that could pave the way to new applications have been found.

Authors: Ibba, F; Capurro, P; Garbarino, S; Anselmo, M; Moni, L

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: American Chemical Society
• Journal: Organic Letters
• Volume: 20
• Issue: 4
• Pages: 1098-1101
• Publication date: 2018-01-30
• Acceptance date: 2018-01-25
• DOI: 10.1021/acs.orglett.8b00009
• EISSN: 1523-7052
• ISSN: 1523-7060
• Pmid: 29381369
• Language: English