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. 2023 Oct 13;25(40):7310-7315.
doi: 10.1021/acs.orglett.3c02636. Epub 2023 Oct 4.

Regioselective Decarboxylative Transformations of Tetrahydro-β-carboline-1-carboxylic Acid: Reagent Controlled Selectivity toward Alkynylated or Enaminone Products

Arka Das  1 , Christine Jonathan  1 , Rana Saha  1 , Md Imran Ahmed  1 , Subhendu Bhowmik  1
Affiliations

Regioselective Decarboxylative Transformations of Tetrahydro-β-carboline-1-carboxylic Acid: Reagent Controlled Selectivity toward Alkynylated or Enaminone Products

Arka Das et al. Org Lett. .

Abstract

A one-pot, regioselective decarboxylative alkynylation of tetrahydro-β-carboline-1-carboxylic acid under peroxide-free condition is reported. The reaction is highly selective for the 1-position over the 3-position of tetrahydro-β-carboline. The reaction can afford alkynylated or enaminone products depending on the reagent. The reaction proceeds through sequential decarboxylative iminium ion formation followed by an alkynylation and oxidative rearrangement cascade.

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