Abstract
The catalytic asymmetric Friedel–Crafts reaction of indoles with nitrodienes and 2-propargyloxy-β-nitrostyrenes was systematically investigated with diphenylamine-linked bis(oxazoline)–Zn(OTf)2 complexes. Moderate to good enantioselectivities were obtained with both kinds of substrates (up to 89 % ee for nitrodienes and up to 93 % ee for β-nitrostyrene derivatives). Further transformation of the corresponding Friedel–Crafts alkylation product of indole with 2-propargyloxy-β-nitrostyrene was carried out to give the chiral isoxazolobenzoxepane derivative, which is of medicinal chemistry interest, with retained enantiomeric purity.
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