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. 2018 Sep 4;23(9):2251.
doi: 10.3390/molecules23092251.

One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones

Xin Huang  1 , Weizhao Zhao  2 , Xiaofeng Zhang  3 , Miao Liu  4 , Stanley N S Vasconcelos  5 , Wei Zhang  6
Affiliations

One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones

Xin Huang et al. Molecules. .

Abstract

A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

Keywords: Michael addition; Robinson annulation; cyclohexenone; fluorination; organocatalysis; α-fluoro-β-keto ester.

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Conflict of interest statement

The authors declare no conflicts of interest

Figures

Figure 1
Figure 1
Bio-active fluorinated cyclohexenones.
Scheme 1
Scheme 1
Robinson annulation-based one-pot synthesis.
Scheme 2
Scheme 2
One-pot synthesis of 6-fluorocyclohex-2-en-1-ones 3.
Scheme 3
Scheme 3
One-pot synthesis of 4,6-difluorocyclohexanones 4.
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