AI Article Synopsis
- A highly efficient method using Ir-catalyzed asymmetric hydrogenation allows for the transformation of racemic β-keto lactams into optically active β-hydroxy lactams through dynamic kinetic resolution.
- The Ir-SpiroSAP catalyst achieves high yields (87-99%) and excellent selectivity in enantiomers and diastereomers (83-99.9% ee, syn/anti ratios of 97:3 to >99:1) while requiring low amounts of catalyst and mild conditions.
- This technique has been successfully utilized to synthesize a chiral intermediate for the fluoroquinolone antibiotic premafloxacine.
Article Abstract
A highly efficient Ir-catalyzed asymmetric hydrogenation of racemic β-keto lactams via dynamic kinetic resolution (DKR) for the synthesis of optically active β-hydroxyl lactams has been described. With the Ir-SpiroSAP catalyst, a series of racemic β-keto lactams including β-keto γ-, δ-, and ε-lactams were hydrogenated to chiral β-hydroxy lactams in high yields (87-99%) with excellent enantio- and diastereoselectivity (83-99.9% ee, syn/anti: 97:3->99:1) at low catalyst loading under mild reaction conditions. This efficient method has been successfully applied in the synthesis of the chiral intermediate of fluoroquinolone antibiotic premafloxacine.
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| http://dx.doi.org/10.1021/acs.orglett.6b03397 | DOI Listing |
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