ChemInform Abstract: Preparation of Optically Enriched 3‐Hydroxy‐3,4‐dihydroquinolin‐2(1H)‐ones by Heterogeneous Catalytic Cascade Reaction over Supported Platinum Catalyst.

Progress in the Chemistry of Tetrahydroquinolines

“…Szőllősi and co-workers showed that 2-nitrophenylpyruvates 954 could be transformed into 3-hydroxy-3,4-dihydroquinolin-2­(1 H )-ones 955 in enantioselectivities up to 90% by catalytic hydrogenation of both the nitro and keto groups using a Pt catalyst in the presence of a Cinchona alkaloid derivative 956 , followed by spontaneous lactonization (Scheme ). The same group later disclosed a detailed study of the influence of reaction conditions on this asymmetric heterogeneous domino reaction…”

“…408 Szollosi and coworkers showed that 2-nitrophenylpyruvates 954 could be transformed into 3-hydroxy-3,4-dihydroquinolin-2(1H)-ones 955 in enantioselectivities up to 90% by catalytic hydrogenation of both the nitro and keto groups using a Pt catalyst in the presence of a Cinchona alkaloid derivative 956, followed by spontaneous lactonization (Scheme 252). 410 The same group later disclosed a detailed study of the influence of reaction conditions on this asymmetric heterogeneous domino reaction. 411 The enantioselective synthesis of chiral 2-carboxytetrahydroquinoline derivatives 958 was achieved by Zhu and Zhou from the diazo derivatives 957 in the presence of a chiral species generated in situ from copper(II) chloride, sodium tetrakis[3,5bis(trifluoromethyl)phenyl]borate (NaBAr F ), and chiral spirobisoxazoline ligands 959 (Scheme 253).…”