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

Xin Huang; Weizhao Zhao; Xiaofeng Zhang; Miao Liu; Stanley  N. S. Vasconcelos; Wei Zhang

doi:10.3390/molecules23092251

Molecules (Sep 2018)

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

Xin Huang,
Weizhao Zhao,
Xiaofeng Zhang,
Miao Liu,
Stanley N. S. Vasconcelos,
Wei Zhang

Affiliations

Xin Huang: College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China
Weizhao Zhao: College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China
Xiaofeng Zhang: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
Miao Liu: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
Stanley N. S. Vasconcelos: Departamento de Farmácia, Universidade de São Paulo, Av. Prof. Lineu Prestes, 580 São Paulo, SP 05508-000, Brazil
Wei Zhang: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA

DOI: https://doi.org/10.3390/molecules23092251
Journal volume & issue: Vol. 23, no. 9
p. 2251

Abstract

Read online

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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

About the journal

Abstract

Keywords