Recent Advances in the Application of α-Phenylethylamine (α-PEA) in the Preparatic of Enantiopure Compounds

摘要

Mostly as a consequence of the increased interest in the production of enantiomerically pure compounds by the pharmaceutical and agrochemical industries, the chemistry community has intensified its efforts to develop more efficient ways to obtain chiral products with the desired configuration. In this regard, α-phenylethylamine (α-PEA. 1-phenylethylamine, 1-phenylethanamine, α-methylbenzenemethanamine, α-methylbenzylamine, α-aminoethylbenzene, CH3CH(Ph)NH2) has emerged as an important chiral reagent principally because of its' low price, accessibility in both enantiomeric forms, and facile introduction and removal in most asymmetric syntheses. Two reviews appeared in the late 1990s on the use of α-PEA in the preparation of enantioenriched compounds. However, a significant number of new developments have been reported in the last decade, which warrants an update on the more significant advances in the area that were reported between 2000 and early 2010. This review focuses on the applications of α-PEA as a chiral ligand for asymmetric catalysis, as a chiral auxiliary in the resolution of racemates, and as a chiral reagent in the stereodifferentiation of prochiral substrates, as well as on its incorporation into novel organocatalysts.