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Volumn 49, Issue 42, 2010, Pages 7782-7785

Enantioselective Lewis acid catalysis in intramolecular [2+2] photocycloaddition reactions of coumarins

Author keywords

Chirality; Cycloadditions; Enantioselectivity; Lewis acids; Photochemistry

Indexed keywords

[2 + 2] PHOTOCYCLOADDITION; CHIRAL LEWIS ACID; CYCLOADDITIONS; ENANTIOSELECTIVE; LEWIS ACID; LEWIS ACID CATALYSIS; PHOTOCHEMISTRY; STEREO-SELECTIVE; STEREOGENIC CENTERS;

EID: 78249281044     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003619     Document Type: Article
Times cited : (129)

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    • In the UV/Vis spectrum of complex 57d in dichloromethane at c=0.5 mm there was no significant bathochromic shift as compared to the parent coumarin 5. Additional bands at longer wavelength were not observed
    • In the UV/Vis spectrum of complex 57d in dichloromethane at c=0.5 mm there was no significant bathochromic shift as compared to the parent coumarin 5. Additional bands at longer wavelength were not observed.
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    • One reviewer has suggested that the E/Z isomerization may occur as a result of photoinduced electron transfer (PET) from the alkene to the excited complex 87d. Indeed, the facile E/Z isomerization of radical cations, which are photochemically generated from alkenes is well precedented, e.g.: D. R. Arnold, S. A. Mines, Can. J. Chem. 1989, 67, 689-690. Currently this reaction pathway cannot be ruled out and should be considered. Triplet quenching studies are under way to support the suggested triplet process
    • One reviewer has suggested that the E/Z isomerization may occur as a result of photoinduced electron transfer (PET) from the alkene to the excited complex 87d. Indeed, the facile E/Z isomerization of radical cations, which are photochemically generated from alkenes is well precedented, e.g.: D. R. Arnold, S. A. Mines, Can. J. Chem. 1989, 67, 689-690. Currently this reaction pathway cannot be ruled out and should be considered. Triplet quenching studies are under way to support the suggested triplet process.
    • (1989) Can. J. Chem. , vol.67 , pp. 689-690
    • Arnold, D.R.1    Mines, S.A.2


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