Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition

Jianyu Zhang, Xi Wang and Tao Xu ()
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Jianyu Zhang: Ocean University of China
Xi Wang: Ocean University of China
Tao Xu: Ocean University of China

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract To the best of our knowledge, bridgehead carbon benzofused-bridged ring systems have previously not been accessible to the synthetic community. Here, we describe a formal type-II [4 + 4] cycloaddition approach that provides fully sp2-carbon embedded anti-Bredt bicyclo[5.3.1] skeletons through the Rh-catalyzed C1–C8 activation of benzocyclobutenones (BCBs) and their coupling with pedant dienamides. Variously substituted dienamides have been coupled with BCBs to provide a range of complex bicyclo[5.3.1] scaffolds (>20 examples, up to 89% yield). The bridged rings were further converted to polyfused hydroquinoline-containing tetracycles via a serendipitously discovered transannular 1,5-hydride shift/Prins-like cyclization/Schmidt rearrangement cascade.

Date: 2021
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DOI: 10.1038/s41467-021-23344-0

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