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

作者：Xu Kun; Gilles Thomas; Breit Bernhard^*

来源：Nature Communications, 2015, 6(1): 7616.

DOI：10.1038/ncomms8616

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.

• 出版日期2015-7