Radical-induced expeditious stereoselective synthesis of 2-alkyl 3-allyl trans-2,3-dihydrobenzofurans (TADHBs)

ABSTRACT

A thorough study on radical-induced cyclopropyl ring fragmentation with encompassed olefinic and cyclopropane environment has been performed. Interestingly, the fragmentation has occasioned onto a stereoselective synthesis of 3-allyl trans-2,3-dihydrobenzofurans with impressive yields. The trans-dihydrobenzofurans are present as central core in many molecules of medicinal interest and the present protocol deliver a straight forward access to the embedded molecular architecture.

GRAPHICAL ABSTRACT

KEYWORDS:

• Allyl benzofuran
• cyclopropyl ring cleavage
• dicyclopropane
• radical
• stereoselective

Acknowledgments

SRS thanks to DST-Inspire for fellowship. We acknowledge Dr. Santanab Giri for conducting the DFT studies and P Behera for NMR studies.

Additional information

Funding

We sincerely acknowledge Department of Science and Technology (DST), Govt. of India (Grant Nos. SB/FT/CS-076/2012 and EEQ/2016/000518), BRNS, Govt. of India (Grant No. 2013/20/37C/2/BRNS/2651), and INSPIRE-DST, Govt. of India (Grant No. 04/2013/000751).