Highly enantioselective synthesis of tetrahydrocarbolines via iridium-catalyzed intramolecular Friedel-Crafts type allylic alkylation reactions.

Org Lett

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

Published: December 2013

AI Article Synopsis

  • A new method for creating substituted tetrahydrocarbolines has been developed using Ir-catalyzed intramolecular reactions.
  • This process shows high selectivity for the desired molecule and works well under mild conditions.
  • It also utilizes a chiral ligand that is easy to obtain, making the synthesis more practical.

Article Abstract

A highly enantioselective synthesis of substituted tetrahydrocarbolines via Ir-catalyzed Friedel-Crafts type intramolecular asymmetric allylic alkylation of 2-indolyl allyl carbonates has been developed. This strategy features excellent chemoselectivity and enantioselectivity, mild reaction conditions, and an easily accessed chiral ligand.

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http://dx.doi.org/10.1021/ol4027717DOI Listing

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