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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 5
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Original Articles

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

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Pages 574-581 | Received 31 Aug 2017, Published online: 24 Jan 2018
 

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

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).

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