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The au(I) catalyzed activation of allenamides and their subsequent transformation into chromanes: a method for the regiocontrolled addition to the alpha- and gamma-positions of the allene unit

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posted on 02.03.2015 by Natasha H. Slater, Natalie J. Brown, Mark Elsegood, Marc Kimber
Au(I) activation of allenamides in the presence of phenols leads to the formation of chromanes in moderate to good yields. This catalytic process is dependent on the counterion which facilitates the activation of the in situ formed imine. Furthermore, this iminium can be intercepted by trimethylallyl silane, via the Hosomi–Sakurai reaction, giving a formal procedure for the regioselective intermolecular addition of two carbon nucleophiles to an allenamide at the α- and γ-positions.

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School

  • Science

Department

  • Chemistry

Published in

ORGANIC LETTERS

Volume

16

Issue

17

Pages

4606 - 4609 (4)

Citation

SLATER, N.H. ... et al, 2014. The au(I) catalyzed activation of allenamides and their subsequent transformation into chromanes: a method for the regiocontrolled addition to the alpha- and gamma-positions of the allene unit. Organic Letters, 16 (17), pp.4606-4609.

Publisher

© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2014

Notes

This definitive published version of this article is available from: http://dx.doi.org/10.1021/ol502178v

ISSN

1523-7060

Language

en

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