Chemo- and stereoselective intermolecular [2 + 2] photocycloaddition of conjugated dienes using colloidal nanocrystal photocatalysts
نویسندگان
چکیده
منابع مشابه
Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction.
2-Quinolone-4-carboxamide derived from (S)-proline, which exists as a mixture of two diastereomers before crystallization, converged to a single diastereomer by crystallization (CIDT), and the homochirality was transferred by a intermolecular 2 + 2 photocycloaddition reaction with high optical activity.
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Short synthetic sequences commencing with the photosensitized [2 + 2]-cycloaddition reactions of maleic anhydride with either allyl alcohol or propargyl alcohol have been elaborated to provide access to 1,2,3-trisubstituted cyclobutanes with three differentiated one-carbon substituents and complementary stereochemical patterns. These intermediates were used to prepare three discrete stereo- and...
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The photocycloaddition of vinylcyclopropanes to C60 yields stereospecifically a five-membered [60]fullerene adduct. These results suggest a biradical intermediate of the [2 + 2] photocycloaddition between dienes or arylalkenes and C60. An electron transfer between the triplet excited state of C60 and the unsaturated substrates precedes the formation of the intermediate.
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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...
متن کاملEnantioselective Intermolecular [2+2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (−)-Grandisol
The intermolecular [2+2] photocycloaddition of typical cyclic α,β-unsaturated enones, such as 2-cyclohexenone, with olefins was performed in moderate to good yields (42-82%) and with high enantioselectivity (82%-96% ee). An unusual substitution pattern at the chiral oxazaborolidine-AlBr3 Lewis acid complex that promotes the reaction was found to be crucial for the success of the reaction. The m...
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ژورنال
عنوان ژورنال: Chem Catalysis
سال: 2021
ISSN: 2667-1093
DOI: 10.1016/j.checat.2021.02.001