Electronically-controlled diastereoselective synthesis of spirocycles via [4 + 2] cycloaddition of 2-arylidene-1-indenones with benzyne

Subhasish Ray; Anup Kumar Yadav; Saurabh Singh; Monish Arbaz Ansari; Maya Shankar Singh

doi:10.1039/d3ob00417a

Electronically-controlled diastereoselective synthesis of spirocycles via [4 + 2] cycloaddition of 2-arylidene-1-indenones with benzyne

Org Biomol Chem. 2023 May 24;21(20):4195-4199. doi: 10.1039/d3ob00417a.

Authors

Subhasish Ray¹, Anup Kumar Yadav¹, Saurabh Singh¹, Monish Arbaz Ansari¹, Maya Shankar Singh¹

Affiliation

¹ Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India. mssingh@bhu.ac.in.

PMID: 37132431
DOI: 10.1039/d3ob00417a

Abstract

A one-pot electronically controlled [4 + 2] cycloaddition reaction of in situ generated benzyne with 2-arylidene-1-indenone is unveiled to construct novel spirocyclic frameworks in a regio- and diastereoselective fashion. This protocol features operational simplicity, good functional group tolerance and avoids the use of metal catalysts and external additives. This methodology has extended the synthetic application of 2-arylidene-1-indenones enabling easy access to valuable 10'H-spiro[indene-2,9'-phenanthren]-1(3H)-ones in good yields.