Chiral Amine Synthesis 2010
DOI: 10.1002/9783527629541.ch6
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Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Abstract: This chapter focuses specifically on the synthesis of amines of the form HNR Ã R 1 , NR Ã R 1 R 2 , and HN(X)R Ã (R Ã ¼ chiral alkyl group; R 1 , R 2 ¼ alkyl or aryl groups; X ¼ heteroatom such as N, S, or P) via the asymmetric hydrogenation of imines, enamines, and iminiums. Thus, we will discuss the formation of amines that have (i) chirality a to the nitrogen, and (ii) no carbonyl group a to nitrogen. Many reported examples of this reaction use substrates with C¼N moieties in a ring, so cyclic amines will r… Show more

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Cited by 8 publications
(2 citation statements)
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“…Until recently, transition-metal-mediated homogeneous catalysis and organo-catalytic methods were the main chemical strategies for the enantioselective reductions. , However, the application of expensive and toxic metals and the requirement of several deprotection steps are the major challenges faced by chemical methods. , Also, chemically catalyzed imine hydrogenation methods require the starting ketone to react with the activated groups of nitrogen sources …”
Section: Imine Reductases (Ireds)mentioning
confidence: 99%
“…Until recently, transition-metal-mediated homogeneous catalysis and organo-catalytic methods were the main chemical strategies for the enantioselective reductions. , However, the application of expensive and toxic metals and the requirement of several deprotection steps are the major challenges faced by chemical methods. , Also, chemically catalyzed imine hydrogenation methods require the starting ketone to react with the activated groups of nitrogen sources …”
Section: Imine Reductases (Ireds)mentioning
confidence: 99%
“…Substrates containing an alkoxyl group, such as MeO, i PrO, and CF 3 CH 2 O, were completely converted to the desired products with high enantioselectivities, 90–97% ee. Notably, the substrates bearing N or P heteroatoms, 1q and 1r , could also be hydrogenated to the chiral amine and phosphate with full conversions and excellent enantioselectivities (97% ee and 99.5% ee, respectively), which could be used as chiral auxiliaries, resolving reagents and building blocks for synthesis of a variety of natural products, pharmaceuticals, and biologically active compounds …”
mentioning
confidence: 99%