Streamlined asymmetric α-difunctionalization of ynones

Siyu Peng, Zhaofeng Wang, Linxing Zhang, Xinhao Zhang and Yong Huang ()
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Siyu Peng: Shenzhen Graduate School
Zhaofeng Wang: Shenzhen Graduate School
Linxing Zhang: Shenzhen Graduate School
Xinhao Zhang: Shenzhen Graduate School
Yong Huang: Shenzhen Graduate School

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Ynones are a unique class of structural motifs that show remarkable chemical versatility. Chiral ynones, particularly those possessing an α-stereogenic center, are highly attractive templates for structural diversification. So far, only very limited examples have been reported for asymmetric α-functionalization of ynones. Asymmetric double α-functionalization of ynones remains elusive. Here we describe a streamlined strategy for asymmetric α-difunctionalization of ynones. We developed a gold-catalyzed multicomponent condensation reaction from a simple ynone, an amine, and an electrophilic alkynylating reagent to generate a 1,2-dialkynyl enamine, a key stable and isolable intermediate. This intermediate can undergo asymmetric fluorination catalyzed by a chiral phosphoric acid derivative. Chiral ynones with an α-quaternary carbon and containing a fluorine and an alkyne can be synthesized in high yield and high ee. The synthetic utility of this method is demonstrated by the synthesis of enantioenriched tri(hetero)arylmethyl fluorides.

Date: 2018
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DOI: 10.1038/s41467-017-02801-9

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