Visible‐Light Photocatalytic Intramolecular Cyclopropane Ring Expansion. Issue 27 (6th June 2017)

• Record Type: Journal Article
• Authors: Luis‐Barrera, Javier; Laina‐Martín, Víctor; Rigotti, Thomas; Peccati, Francesca; Solans‐Monfort, Xavier; Sodupe, Mariona; Mas‐Ballesté, Rubén; Liras, Marta; Alemán, José
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 27(2017)
• Page Start: 7826
• Page End: 7830
• Publication Date: 2017-06-06
• Subjects: density functional calculations -- small ring systems -- photocatalysis -- reaction mechanisms -- ring expansion; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201703334
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Described herein is a new visible‐light photocatalytic strategy for the synthesis of enantioenriched dihydrofurans and cyclopentenes by an intramolecular nitro cyclopropane ring expansion reaction. Mechanistic studies and DFT calculations are used to elucidate the key factors in this new ring expansion reaction, and the need for the nitro group on the cyclopropane. Abstract : Expansion project : A new visible‐light photocatalytic strategy for the synthesis of enantioenriched dihydrofurans and cyclopentenes through a ring expansion process is presented. Mechanistic and computational studies rationalize the key factors of the reaction.