Application of a C-C Bond-Forming Conjugate Addition Reaction in Asymmetric Dearomatization of β-Naphthols

Dongxu Yang; Linqing Wang; Ming Kai; Dan Li; Xiaojun Yao; Rui Wang

doi:10.1002/anie.201503056

Application of a C-C Bond-Forming Conjugate Addition Reaction in Asymmetric Dearomatization of β-Naphthols

Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9523-7. doi: 10.1002/anie.201503056. Epub 2015 Jul 14.

Authors

Dongxu Yang¹, Linqing Wang¹, Ming Kai¹, Dan Li¹, Xiaojun Yao¹, Rui Wang^{2

3}

Affiliations

¹ Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000 (China).
² Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000 (China). wangrui@lzu.edu.cn.
³ State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (China). wangrui@lzu.edu.cn.

PMID: 26173841
DOI: 10.1002/anie.201503056

Abstract

A C-C bond-forming conjugate reaction was successfully applied to the enantioselective dearomatization of β-naphthols. A C(sp2)-C(sp3) bond is formed by using propargylic ketones as reactive partners. Good to excellent Z/E ratios and ee values were obtained by employing an in situ generated magnesium catalyst. Further transformations of the Z-configured C-C double bond in the products were achieved under mild reaction conditions. Moreover, the stereocontrolling element of this magnesium-catalyzed dearomatization reaction was explored by computational chemistry.

Keywords: DFT calculations; arenes; aromaticity; magnesium; naphthols.

Publication types

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

MeSH terms

Ketones / chemistry*
Magnesium / chemistry
Models, Molecular
Naphthols / chemistry*
Stereoisomerism

Substances

Ketones
Naphthols
Magnesium
2-naphthol