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• W2000798758 abstract "The GaCl3-catalyzed [4+1] cycloaddition reactions of α,β-unsaturated ketones with isocyanides leading to lactone derivatives are described. While some other Lewis acids also show catalytic activity, GaCl3 was the most efficient catalyst. The reaction is significantly affected by the structure of both the isocyanides and the α,β-unsaturated ketones. Aromatic isocyanides, especially sterically demanding ones and those bearing an electron-withdrawing group, can be used, but aliphatic isocyanides cannot. The bulkiness of substituents at the β-position of acyclic α,β-unsaturated ketones is an important factor for the reaction to proceed efficiently. Generally, the more the bulky substituent, the higher is the yield. The reaction of α,β-unsaturated ketones bearing geminal substituents at the β-position gave the corresponding products in high yields. In monosubstituted derivatives, the yields are relatively low. However, substrates having a bulky substituent, such as a tert-Bu group, at the β-position give high yields. Bulkiness is also required in cyclic α,β-unsaturated ketones, but the effect is small. In alkyl vinyl ketones, the reactivity decreased with the steric bulk of the alkyl group. In aryl vinyl ketones, the presence of an electron-donating group on the aromatic ring decreases the reactivity. The success of the catalysis can be attributed to the low affinity of GaCl3 toward heteroatoms, compared with usual Lewis acids." @default.
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• W2000798758 date "2004-12-04" @default.
• W2000798758 modified "2023-10-16" @default.
• W2000798758 title "Catalytic [4+1] Cycloaddition of α,β-Unsaturated Carbonyl Compounds with Isocyanides" @default.
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• W2000798758 doi "https://doi.org/10.1021/ja0450206" @default.
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