Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation | Zendy

Andreas Tröster | Zendy; Rafael Alonso | Zendy; Andreas Bauer | Zendy; Thorsten Bach | Zendy

Open Access

Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation

Author(s) -

Andreas Tröster,

Rafael Alonso,

Andreas Bauer,

Thorsten Bach

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.6b03221

Subject(s) - chemistry , enantioselective synthesis , intermolecular force , catalysis , photochemistry , cyclobutane , enantiomer , combinatorial chemistry , substrate (aquarium) , stereochemistry , medicinal chemistry , organic chemistry , molecule , ring (chemistry) , oceanography , geology

In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.

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