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Molecules 2018, 23(9), 2251; https://doi.org/10.3390/molecules23092251

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

1
College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China
2
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
3
Departamento de Farmácia, Universidade de São Paulo, Av. Prof. Lineu Prestes, 580 São Paulo, SP 05508-000, Brazil
*
Authors to whom correspondence should be addressed.
Received: 4 August 2018 / Revised: 29 August 2018 / Accepted: 31 August 2018 / Published: 4 September 2018
(This article belongs to the Special Issue Stereogenic Centers)
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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. View Full-Text
Keywords: organocatalysis; fluorination; α-fluoro-β-keto ester; Michael addition; Robinson annulation; cyclohexenone organocatalysis; fluorination; α-fluoro-β-keto ester; Michael addition; Robinson annulation; cyclohexenone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Huang, X.; Zhao, W.; Zhang, X.; Liu, M.; Vasconcelos, S.N.S.; Zhang, W. One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones. Molecules 2018, 23, 2251.

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