Application of Benzofuran-Derived Azadienes as Two-Carbon Building Blocks in Annulations: Chemo- and Diastereoselective Construction of Spiro-Benzofuran Scaffolds

§ These authors contributed equally to this work.

Abstract

A base-promoted (2+4) annulation of benzofuran-derived azadienes with para-quinone methide derivatives has been established, which afforded spiro-benzofuran derivatives in generally high yields (57–97%) and with good diastereoselectivities (85:15 to >95:5 dr). This reaction not only represents the first application of benzofuran-derived azadienes as two-carbon building blocks in annulations, but also provides an efficient protocol for the construction of spiro-benzofuran scaffolds with chemoselectivity and high diastereoselectivity. This approach will enrich the chemistry of benzofuran-derived azadiene-involved reactions.

Key words

benzofuran-derived azadiene - para-quinone methide - annulation - spiro-benzofuran - diastereoselectivity

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1919
• 19a CCDC 2007585 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 19b See the Supporting Information for details.