- Preparation and Reactivity of New β-Nitrogen-Functionalized Vinylic Organolithium Compounds from Secondary Aliphatic Allylamines
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Two new types of β-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group.The monoanionic intermediates 4, stable at -80 deg C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction.Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27.Moreover, dianionic derivatives 30,33 can be prepared directly by bromine-lithium exchange when the β-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered.Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.
- Barluenga, Jose,Canteli, Rosa-Maria,Florez, Josefa
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- Switchable Copper-Catalyzed Cascade Synthesis of Thiazolidine-2-thiones and Thiazole-2(3 H)-thiones
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A novel copper-catalyzed cascade synthesis of thiazolidine-2-thiones from N-(2-bromoallyl)amines and carbon disulfide has been developed. The procedure combines carbamodithioic acid formation and copper-catalyzed intramolecular S-vinylation in one sequence. By elevating the temperature, the one-pot reaction efficiently affords thiazole-2(3H)-thiones in moderate to good yields.
- Weng, Jian-Quan,Yue, Bin-Jie,Xu, Meng,Yang, Yu-Kun,Jin, Hong-Wei
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p. 2991 - 2996
(2015/09/28)
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