ol301559k_si_002.cif (18.13 kB)

FeCl3‑Catalyzed Stereoselective Construction of Spirooxindole Tetrahydroquinolines via Tandem 1,5-Hydride Transfer/Ring Closure

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posted on 17.08.2012, 00:00 by Yan-Yan Han, Wen-Yong Han, Xue Hou, Xiao-Mei Zhang, Wei-Cheng Yuan
An efficient FeCl3-catalyzed stereoselective intramolecular tandem 1,5-hydride transfer/ring closure reaction was developed. The method allows for the formation of structurally diverse spirooxindole tetrahydroquinolines in high yields (up to 98%) with good to excellent levels of diastereoselectivity (up to 99:1 dr). The catalytic enantioselective variant of this process was also investigated preliminarily with a chiral BINOL-derived phosphoric acid.