Enantioselective Synthesis of 3a-Amino-Pyrroloindolines by Copper-Catalyzed Direct Asymmetric Dearomative Amination of Tryptamines.

Angew Chem Int Ed Engl

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China).

Published: January 2016

AI Article Synopsis

  • A new method for amination of tryptamines using DPH and a CuBr-bisoxazoline catalyst was developed, leading to compounds called 3a-amino-pyrroloindolines with high enantioselectivity.
  • This reaction occurs under mild conditions, making it a potentially practical approach in organic synthesis.
  • The method was successfully applied in the total synthesis of (-)-psychotriasine, showing its synthetic utility and efficiency.

Article Abstract

A direct asymmetric dearomative amination of tryptamines with O-(2,4-dinitrophenyl)hydroxylamine (DPH) was achieved using CuBr-bisoxazoline complex as a catalyst, affording 3a-amino-pyrroloindolines in good to excellent enantioselectivity under mild reaction conditions. Furthermore, the synthetic value of this method was demonstrated in the total synthesis of (-)-psychotriasine in a highly concise manner.

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http://dx.doi.org/10.1002/anie.201508570DOI Listing

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