Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 26137886.
- Also identified by DOI 10.1038/ncomms8616 and PMC identifier 4506507.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
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.
Medical subject headings
- Alkadienes
- Allyl Compounds
- Hydrazines
- Indoles