Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2 carboxylates.

نویسندگان

  • Sabilla Zhong
  • Martin Nieger
  • Angela Bihlmeier
  • Min Shi
  • Stefan Bräse
چکیده

We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-vinyl indoles with imino esters in dichloromethane at room temperature after 1 h of reaction time. A variety of these compounds could be synthesized in up to 70% yield and 99% ee, and they were experimentally and computationally analyzed regarding their relative and absolute stereochemistry.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 12 20  شماره 

صفحات  -

تاریخ انتشار 2014