Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes

Xiying Zhang; Wangbin Wu; Weidi Cao; Han Yu; Xi Xu; Xiaohua Liu; Xiaoming Feng

doi:10.1002/anie.201914151

Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes

Angew Chem Int Ed Engl. 2020 Mar 16;59(12):4846-4850. doi: 10.1002/anie.201914151. Epub 2020 Jan 30.

Authors

Xiying Zhang¹, Wangbin Wu¹, Weidi Cao¹, Han Yu¹, Xi Xu¹, Xiaohua Liu¹, Xiaoming Feng¹

Affiliation

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.

PMID: 31930609
DOI: 10.1002/anie.201914151

Abstract

Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N'-dioxide/Ni^II complex catalyst with Ag₂ O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee). Furthermore, a range of different radical-mediated oxidation/elimination or epoxide ring-opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.

Keywords: Lewis acid; alkenes; asymmetric catalysis; oxidation; radicals.

Abstract

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