Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides

Babli K. Jha; Jaggaraju Prudhviraj; Prathama S. Mainkar; Nagender Punna; Srivari Chandrasekhar

doi:10.1039/D0RA08289A

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Diastereoselective synthesis of CF₃-dihydrobenzofurans by [4+1] annulation of in situ-generated CF₃-o-quinone methides and sulfur ylides†

Babli K. Jha,^ab Jaggaraju Prudhviraj,^a Prathama S. Mainkar,

^ab Nagender Punna

*^ab and Srivari Chandrasekhar

*^ab

Author affiliations

* Corresponding authors

^a Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
E-mail: srivaric@iict.res.in, nagenderpunna@iict.res.in

^b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India

Abstract

An efficient and highly diastereoselective synthesis of CF₃-dihydrobenzofurans by the reaction of in situ-generated CF₃-oQMs in the presence of a base with sulphur ylides is put forward. The generality of the present developed method was well studied with diverse substrates to access the corresponding products in excellent yields. The highly reactive CF₃-oQM has been utilized first time for the annulation reaction.

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DOI: https://doi.org/10.1039/D0RA08289A
Article type: Paper
Submitted: 26 Aug 2020
Accepted: 29 Sep 2020
First published: 20 Oct 2020
This article is Open Access

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RSC Adv., 2020,10, 38588-38591

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Diastereoselective synthesis of CF₃-dihydrobenzofurans by [4+1] annulation of in situ-generated CF₃-o-quinone methides and sulfur ylides

B. K. Jha, J. Prudhviraj, P. S. Mainkar, N. Punna and S. Chandrasekhar, RSC Adv., 2020, 10, 38588 DOI: 10.1039/D0RA08289A

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