Tuning Vinylethylene Carbonates into [4 + 2] Cycloaddition via Silylation and Vinylogous Peterson Elimination

Wei Feng; Li Xu; Deng-Yuan Li; Pei-Nian Liu

doi:10.1021/acs.orglett.0c01690

Tuning Vinylethylene Carbonates into [4 + 2] Cycloaddition via Silylation and Vinylogous Peterson Elimination

Org Lett. 2020 Jul 2;22(13):5094-5098. doi: 10.1021/acs.orglett.0c01690. Epub 2020 Jun 17.

Authors

Wei Feng¹, Li Xu¹, Deng-Yuan Li¹, Pei-Nian Liu¹

Affiliation

¹ Shanghai Key Laboratory of Functional Materials Chemistry, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Key Laboratory for Advanced Materials and School of Chemistry and Molecular Engineering, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, China.

PMID: 32551710
DOI: 10.1021/acs.orglett.0c01690

Abstract

Vinylethylene carbonates have been extensively used to trigger [3 + n] or [5 + n] cycloaddition via the formation of η³-allylic intermediates, while the important [4 + n] cycloaddition has not been explored yet. Here, we report a new strategy to convert vinylethylene carbonates into 4-(trimethylsilyl)but-2-en-1-ols, which can readily undergo [4 + 2] cycloaddition by in situ formation of 1,3-dienes. This novel reaction involves [Pd^II]-catalyzed decarboxylative silylation, [Fe^III]-catalyzed vinylogous Peterson elimination, and subsequent [4 + 2] cycloaddition to afford a multisubstituted cyclohexa-1,4-diene skeleton.