Abstract
Development of metal-free strategies for stereoselective hydrogenation of unsaturated substrates is of particular interest in asymmetric synthesis. The emerging chemistry of frustrated Lewis pairs ...
Highlights
Chiral amines, those bearing α-stereogenic carbon atoms, are widely used intermediates in the production of pharmaceuticals, agrochemicals, and fine chemicals
To gain more insight into the nature of molecular interactions responsible for the stereoselectivity of frustrated Lewis pairs (FLPs)-catalyzed hydrogenation, in our present work we investigated a reaction that is frequently used as a test case in the evaluation of developed catalysts, namely, the direct hydrogenation of imine (E)-N-(1phenylethylidene)-aniline
HT refers to hydride transfer from BH− to the prochiral carbon of imH+
Summary
Those bearing α-stereogenic carbon atoms, are widely used intermediates in the production of pharmaceuticals, agrochemicals, and fine chemicals. The development of effective methods for enantioselective synthesis of these compounds is of high interest.[1] Among the available synthetic strategies, the asymmetric hydrogenation of prochiral imines and enamines by the direct use of H2 as the hydrogen source represents a promising atom-economic approach.[2] A variety of transition metal (TM) complexes comprising chiral organic ligands have been developed, and some of them have proved to be efficient catalysts for direct enantioselective imine hydrogenations. Iridium complexes are known to be powerful hydrogenation catalysts; achieving very high enantioselectivities for a wide range of substrates remains challenging.[3]. These so-called frustrated Lewis pairs (FLPs)[8] were shown to catalyze various unsaturated organic substrates[9] even under watertolerant conditions.[10]
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