Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 20, Pages 2979-2986Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707205
Keywords
benzofuran-derived azadiene; para-quinone methide; annulation; spiro-benzofuran; diastereoselectivity
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Funding
- National Natural Science Foundation of China [21772069, 21831007]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
- TAPP
- Undergraduate Students Project of JSNU
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A base-promoted (2+4) annulation of benzofuran-derived azadienes withpara-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.
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