Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates

Linqing Wang; Dongxu Yang; Dan Li; Pengxin Wang; Kezhou Wang; Jie Wang; Xianxing Jiang; Rui Wang

doi:10.1002/chem.201601399

Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates

Chemistry. 2016 Jun 13;22(25):8483-7. doi: 10.1002/chem.201601399. Epub 2016 May 3.

Authors

Linqing Wang¹, Dongxu Yang², Dan Li¹, Pengxin Wang¹, Kezhou Wang¹, Jie Wang¹, Xianxing Jiang³, Rui Wang⁴

Affiliations

¹ Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, P. R. China.
² Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, P. R. China. yangdx@lzu.edu.cn.
³ School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, P. R. China. Jiangxx5@mail.sysu.edu.cn.
⁴ Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, P. R. China. wangrui@lzu.edu.cn.

PMID: 27139904
DOI: 10.1002/chem.201601399

Abstract

A Mg(II) -mediated catalytic asymmetric dearomatization (CADA) reaction of β-naphthols has been developed. The reaction proceeds under ambient temperature and give a series of chiral trisubstituted olefins with good chemoselectivities, Z/E ratios, and excellent enantioselectivities. A fluorinated β-naphthol was designed to generate chiral organofluorine skeletons through the current CADA reaction. Moreover, an interesting tandem cyclization reaction was observed in the following transformation process through an undiscovered intramolecular hydride transfer pathway.

Keywords: cyclization; dearomatization; fluorine; magnesium; naphthols.

Publication types

Research Support, Non-U.S. Gov't