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

ABSTRACT: Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave ?,?-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.

SUBMITTER: Takaki K 

PROVIDER: S-EPMC5588593 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Takaki Ken K   Hino Makoto M   Ohno Akira A   Komeyama Kimihiro K   Yoshida Hiroto H   Fukuoka Hiroshi H  

Beilstein journal of organic chemistry 20170830

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. ...[more]

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