Indoles from 3-Nitropyridinium Salts: A new Route to Chiral Indoles and Indolines

Article abstract of DOI:10.1016/0957-4166(95)00379-7

(S)-1-(1-Methylbenzyl)-2,4,6-trimethylindole was prepared by interaction of (S)-isopropyliden(1-methylbenzyl)amine with 1,2,4,6-tetramethyl-3-nitropyridinium iodide.The indoles thus prepared undergo diastereoselective hydride reduction and debenzylation to afford chiral (S)-2,4,6-trimethylindoline with high yield an optical purity up to 76percent.