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Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives†
Kamal Verma,Irshad Maajid Taily,Prabal Banerjee
Organic & Biomolecular Chemistry Pub Date : 08/16/2019 00:00:00 , DOI:10.1039/C9OB01369E
Abstract

A MgI2 catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of highly functionalized spiro-cyclopentane benzofuran derivatives has been developed. This methodology is appreciated in terms of chemoselectivity and mild reaction conditions. In addition, hydrolysis of one of the N-sulfonyl derivatives offered the corresponding spiro dihydrofuran-3-one derivative in the presence of basic alumina.

Graphical abstract: Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives
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