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Title: 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
Authors: Slater, Natasha H.
Brown, Natalie J.
Elsegood, Mark R.J.
Kimber, Marc C.
Issue Date: 2014
Publisher: © American Chemical Society
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.
Abstract: 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.
Description: This definitive published version of this article is available from: http://dx.doi.org/10.1021/ol502178v
Version: Accepted for publication
DOI: 10.1021/ol502178v
URI: https://dspace.lboro.ac.uk/2134/16851
Publisher Link: http://dx.doi.org/10.1021/ol502178v
ISSN: 1523-7060
Appears in Collections:Published Articles (Chemistry)

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