Trost, Barry M.; Thaisrivongs, David A.; Hartwig, Jan published the artcile< Palladium-Catalyzed Asymmetric Allylic Alkylations of Polynitrogen-Containing Aromatic Heterocycles>, Computed Properties of 152140-65-3, the main research area is cyclohexenylmethyl nitrogen heterocycle enantioselective preparation; enantioselective allylic alkylation cyclohexenyl cyclopentenyl mesityl ester nitrogen heterocycle; trimethylbenzoate ester leaving group enantioselective allylic alkylation reaction.
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.
Journal of the American Chemical Society published new progress about Allylic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent) (esters). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Computed Properties of 152140-65-3.
Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate