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Enantioselective [2 + 2] Photocycloaddition via Iminium Ions: Catalysis by a Sensitizing Chiral Brønsted Acid

Pecho, F. ; Sempere, Y. ; Gramüller, Johannes ; Hörmann, F. M. ; Gschwind, Ruth Maria ; Bach, T.



Abstract

N,O-Acetals derived from α,β-unsaturated β-aryl substituted aldehydes and (1-aminocyclohexyl)methanol were found to undergo a catalytic enantioselective [2 + 2] photocycloaddition to a variety of olefins (19 examples, 54–96% yield, 84–98% ee). The reaction was performed by visible light irradiation (λ = 459 nm). A chiral phosphoric acid (10 mol %) with an (R)-1,1′-bi-2-naphthol (binol) backbone ...

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