Enantioselective Construction of Bicyclic Pyran and Hydrindane Scaffolds via Intramolecular Rauhut–Currier Reactions Catalyzed by Thiourea-Phosphines

Highly enantioselective intramolecular RC reactions via desymmetrization of cyclohexadienones have been developed. By employing cyclohexadienones with a flexible ether or alkyl group linked internal enone moiety, optically enriched bicyclic pyran and hydrindane skeletons were constructed. Bifunction...

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Published inACS catalysis Vol. 8; no. 9; pp. 8810 - 8815
Main Authors Li, Kaizhi, Jin, Zhichao, Chan, Wai-Lun, Lu, Yixin
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.09.2018
Subjects
bifunctional phosphine
desymmetrization
thiourea
Rauhut−Currier reaction
hydrindane
bicyclic pyran
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Summary:Highly enantioselective intramolecular RC reactions via desymmetrization of cyclohexadienones have been developed. By employing cyclohexadienones with a flexible ether or alkyl group linked internal enone moiety, optically enriched bicyclic pyran and hydrindane skeletons were constructed. Bifunctional phosphine catalysts bearing a thiourea moiety were found to effectively promote the reaction, and preliminary studies suggest that the hydrogen-bonding interaction between thiourea and carbonyl group is crucial and facilitates the otherwise flexible backbones to undergo the desired cyclization.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b02706