Spin‐Selectivity in Photochemistry: A Tool for Organic Synthesis

Griesbeck, Axel G.

doi:10.1002/chin.200324244

ChemInform

2003

DOI: 10.1002/chin.200324244

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Spin‐Selectivity in Photochemistry: A Tool for Organic Synthesis

Axel G. Griesbeck¹

Abstract: For Abstract see ChemInform Abstract in Full Text.

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“…Phosphoric acid 6f thus not only provides the required energy to promote the substrates to the triplet state but also guarantees the required enantioface differentiation. Remarkably, the enantioselective reactions display a higher degree of diastereoselectivity 22 than related reactions with achiral iminium ions which were used to prepare racemic cyclobutanes 12 for comparison. For example, the d.r.…”

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confidence: 99%

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

et al. 2021

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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 served as the catalyst. The acid displays two thioxanthone groups attached to position 3 and 3′ of the binol core via a meta -substituted phenyl linker. NMR studies confirmed the formation of an iminium ion which is attached to the acid counterion in a hydrogen-bond assisted ion pair. The catalytic activity of the acid rests on the presence of the thioxanthone moieties which enable a facile triplet energy transfer and an efficient enantioface differentiation.

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

et al. 2021

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The Paternò–Büchi reaction –a comprehensive review

D’Auria

2019

Photochem Photobiol Sci

112

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Spin‐Selectivity in Photochemistry: A Tool for Organic Synthesis

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 52 publications

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

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

The Paternò–Büchi reaction –a comprehensive review

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