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Asymmetric Synthesis of N-allylic Indoles Via Regio- and Enantioselective Allylation of Aryl Hydrazines
Kun Xu
Thomas Gilles
Bernhard Breit
出版
Universität
, 2015
URL
http://books.google.com.hk/books?id=an-MtQEACAAJ&hl=&source=gbs_api
註釋
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