Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines

Kun Xu, Thomas Gilles and Bernhard Breit ()
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Kun Xu: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg
Thomas Gilles: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg
Bernhard Breit: Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg

Nature Communications, 2015, vol. 6, issue 1, 1-7

Abstract: Abstract The asymmetric synthesis of N-allylic indoles is important for natural product synthesis and pharmaceutical research. The regio- and enantioselective N-allylation of indoles is a true challenge due to the favourable C3-allylation. We develop here a new strategy to the asymmetric synthesis of N-allylic indoles via rhodium-catalysed N-selective coupling of aryl hydrazines with allenes followed by Fischer indolization. The exclusive N-selectivities and good to excellent enantioselectivities are achieved applying a rhodium(I)/DTBM-Segphos or rhodium(I)/DTBM-Binap catalyst. This method permits the practical synthesis of valuable chiral N-allylated indoles, and avoids the N- or C-selectivity issue.

Date: 2015
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DOI: 10.1038/ncomms8616

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