On August 17, 2011, Trost, Barry M.; Thaisrivongs, David A.; Hartwig, Jan published an article.Electric Literature of 34413-35-9 The title of the article was Palladium-Catalyzed Asymmetric Allylic Alkylations of Polynitrogen-Containing Aromatic Heterocycles. And the article contained the following:
Nonracemic cyclohexenylmethyl- and cyclopentenylmethyl-substituted nitrogen heterocycles such as I are prepared in 44-93% yields and in 75->99% ee by enantioselective allylic alkylation reactions of cyclohexenyl and cyclopentenyl trimethylbenzoates with methyl-substituted nitrogen heterocycles such as 2-methylpyrazine in the presence of bis(allylpalladium chloride) and a nonracemic dibenzamidodibenzobicyclooctane ligand. Methylated nitrogen-containing aromatic heterocycles such as 2-methylpyrazine, 2-methylpyrimidine, 3-methyl-6-phenylpyridazine, 2-methylquinoxaline, and 1-benzyl-2-methylbenzimidazole are effective reactants. 5,6,7,8-Tetrahydroquinoxaline also undergoes enantioselective allylic alkylation with a cyclohexenyl trimethylbenzoate to give cyclohexenyl tetrahydroquinoxaline II in 99% yield, >99% ee, and in 81:19 diastereoselectivity. The mesityl ester, whose steric bulk prevents competitive deacylation of the electrophile from “hard” nucleophiles, is introduced as a new leaving group in allylic alkylation chem. In contrast to previous studies of enantioselective allylic alkylation reactions with pyridine-based substrates, no precomplexation with a Lewis acid is required before deprotonation of the nucleophiles with LiHMDS, underscoring the relative acidity of these electron-deficient nucleophiles. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Electric Literature of 34413-35-9
The Article related to cyclohexenylmethyl nitrogen heterocycle enantioselective preparation, enantioselective allylic alkylation cyclohexenyl cyclopentenyl mesityl ester nitrogen heterocycle, trimethylbenzoate ester leaving group enantioselective allylic alkylation reaction and other aspects.Electric Literature of 34413-35-9
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider