Lefranc, Julien; Minassi, Alberto; Clayden, Jonathan published an article in 2013, the title of the article was Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates.Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate And the article contains the following content:
N-(alkenyl)urea derivatives and N-(alkenyl)carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, the authors show that they will also undergo attack at the β-carbon by organolithium nucleophiles, leading to the products of carbolithiation. The carbolithiation of (E)-(alkenyl)urea and (Z)-(alkenyl)urea derivatives is diastereoselective and N-tert-butoxycarbonyl N-alkenyl carbamates give carbolithiation products that may be deprotected in situ to provide a new connecting route to hindered amines. The title compounds thus formed included rel-N-(4-methoxyphenyl)-N,N’-dimethyl-N’-[(1R,2R)-2-methyl-1-phenylhexyl]urea (I) and related substances, such as carbamate esters, N-methyl-N-(3-methyl-1-phenylbutyl)carbamic acid 1,1-dimethylethyl ester. The synthesis of the target compounds was achieved by a reaction of (butyl)lithium, (tert-butyl)lithium, etc. with N,N’-dimethyl-N-phenyl-N’-(1-phenylethenyl)urea derivatives, [N(E)]-N-(1-phenylethylidene)methanamine, N-[(phenyl)alkenyl]carbamic acid esters. The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
The Article related to carbamate urea carbometalation lithiation stereoselective synthesis, carbamate, carbolithiation, carbometallation, organolithium, stereospecificity, styrene, urea, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Ureas, Carbamic Acids, Guanidines, and Their Sulfur-Containing Analogs and other aspects.Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
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