NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

Takaki Ken

Hino Makoto

Ohno Akira

Komeyama Kimihiro

Yoshida Hiroto

Fukuoka Hiroshi

Beilstein Journal of Organic Chemistry

Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of the coupling products.

Breslow intermediate

N-heterocyclic carbene

ring enlargement

Stetter reaction

vicinal polyketone

eng

Beilstein-Institut

© 2017 Takaki et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc) The definitive version of this article is the electronic one which can be found at: doi:10.3762/bjoc.13.176

[ISSN] 1860-5397

[DOI] 10.3762/bjoc.13.176

[DOI] https://doi.org/10.3762/bjoc.13.176