Catalytic radical cascade cyclization of alkene-tethered enones to fused bicyclic cyclopropanols. Issue 23 (27th October 2021)

• Record Type: Journal Article
• Authors: Xie, Ying; Huang, Wei; Qin, Song; Fu, Shaomin; Liu, Bo
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 23(2021)
• Page Start: 6678
• Page End: 6686
• Publication Date: 2021-10-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01312b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Fused bicyclic cyclopropanols were achieved via an unprecedented HAT-triggered radical cascade reaction of alkene-tethered enones in the presence of an iron catalyst. Abstract : An unprecedented hydrogen atom transfer-triggered intramolecular cascade reaction between alkenes and enones is developed, using Fe(acac)3, PhSiH2 (Oi-Pr) and trimethyl borate, to efficiently construct cis -fused bicyclic cyclopropanols, privileged scaffolds often found in natural products. This mild protocol features unique regio- and stereo-selectivity and impressive functional group tolerability. Mechanistic studies reveal that cyclopropane-containing motifs could be generated through a stepwise radical process rather than the Michael addition reaction.