Jump to main content
Jump to site search

Issue 28, 2017
Previous Article Next Article

Governing effects in the mechanism of the gold-catalyzed cycloisomerization of allenic hydroxylamine derivatives

Author affiliations

Abstract

The formation of chiral heterocycles via cycloisomerization reactions of allene derivatives has gained relevance due to their associated efficiency and atom-economy. The only drawback that keeps these reactions away from being routine synthetic strategies is the control in the regioselectivity (most often 5-endo vs. 6-endo). In this work, we computationally explore the experimental chemistry reported by Krause using N-hydroxy-α-aminoallenes and hydroxylamine ethers as substrates and provide a rationale for the different reactivity observed. The drastic effects observed experimentally when changing the nature of the gold catalyst have also been studied mechanistically. These results are expected to help in the design of improved regioselective protocols for the formation of medium sized chiral heterocycles from allene substrates.

Graphical abstract: Governing effects in the mechanism of the gold-catalyzed cycloisomerization of allenic hydroxylamine derivatives

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 May 2017, accepted on 16 Jun 2017 and first published on 16 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01275F
Citation: Org. Biomol. Chem., 2017,15, 5920-5926
  •   Request permissions

    Governing effects in the mechanism of the gold-catalyzed cycloisomerization of allenic hydroxylamine derivatives

    S. Kiriakidi, O. Nieto Faza, A. Kolocouris and C. S. López, Org. Biomol. Chem., 2017, 15, 5920
    DOI: 10.1039/C7OB01275F

Search articles by author

Spotlight

Advertisements