Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters Article

Kaur, N, Kumar, P, Dutt, S et al. (2022). Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters . JOURNAL OF ORGANIC CHEMISTRY, 87(12), 7905-7918. 10.1021/acs.joc.2c00566

cited authors

  • Kaur, N; Kumar, P; Dutt, S; Banerjee, P

authors

abstract

  • Herein, we report a straightforward one-pot synthesis of tetrahydrofurobenzopyran and tetrahydrofurobenzofuran systems via an in situ ring-expansion of the cyclopropane carbaldehydes followed by a [2 + n] cycloaddition with the quinone derivatives. The transformation not only unveils a new reaction mode of cyclopropane carbaldehydes with quinone methides/esters, but also promotes a step-efficient diastereoselective route to the sophisticatedly fused oxygen tricycles that can be further dehydrogenated to access the valued dihydro-2H-furo[2,3-b]chromene frameworks.

publication date

  • June 17, 2022

published in

Digital Object Identifier (DOI)

start page

  • 7905

end page

  • 7918

volume

  • 87

issue

  • 12