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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
journal contribution
posted on 2015-03-02, 14:46 authored by Natasha H. Slater, Natalie J. Brown, Mark ElsegoodMark Elsegood, Marc KimberMarc KimberAu(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.
History
School
- Science
Department
- Chemistry
Published in
ORGANIC LETTERSVolume
16Issue
17Pages
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 SocietyVersion
- 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
2014Notes
This definitive published version of this article is available from: http://dx.doi.org/10.1021/ol502178vISSN
1523-7060Publisher version
Language
- en