Palladium-catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans via intramolecular trapping of O-ylides with activated alkenes

An efficient palladium catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans has been accomplished in good yield as a single diastereomer. The transformation involves in-situ generation of oxonium ylide from 2-hydroxyphenyl substituted enone and diazo compound followed by intramolecular trapping via Michael addition. Successful integration of the developed method with intramolecular aldol condensation afforded potent dibenzofuran derivatives in good yield. (c) 2021 Elsevier Inc. All rights reserved.

Automated summary

An efficient palladium-catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans has been achieved in good yield as a single diastereomer. The transformation involves in-situ generation of oxonium ylide from 2-hydroxyphenyl substituted enone and diazo compound followed by intramolecular trapping via Michael addition, leading to potent dibenzofuran derivatives in good yield.