Tags

Type your tag names separated by a space and hit enter

Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed by a Chiral Phosphoric Acid.
Chemistry. 2017 Apr 19; 23(22):5381-5385.C

Abstract

An enantioselective arylative dearomatization reaction of β-naphthols with quinone monoimides has been developed for the first time using a chiral phosphoric acid as the catalyst, the desired enantioenriched cyclohexadienones were prepared with excellent yields and enantioselectivities by a domino Michael addition and aromatization process (up to 99 % yield, up to 98 % ee). This process is operationally simple and readily scaled up, as well as a broad substrate scope which includes 1-substituted-2-naphthols with/without 3-substituents. Furthermore, this organocatalytic procedure allows the lowering of catalyst loading to 0.5 mol % without considerable loss in reactivity and enantioselectivity.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an, 710127, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28272764

Citation

Li, Xiao-Qiang, et al. "Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed By a Chiral Phosphoric Acid." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 23, no. 22, 2017, pp. 5381-5385.

Li XQ, Yang H, Wang JJ, et al. Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed by a Chiral Phosphoric Acid. Chemistry. 2017;23(22):5381-5385.

Li, X. Q., Yang, H., Wang, J. J., Gou, B. B., Chen, J., & Zhou, L. (2017). Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed by a Chiral Phosphoric Acid. Chemistry (Weinheim an Der Bergstrasse, Germany), 23(22), 5381-5385. https://doi.org/10.1002/chem.201701015

Li XQ, et al. Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed By a Chiral Phosphoric Acid. Chemistry. 2017 Apr 19;23(22):5381-5385. PubMed PMID: 28272764.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed by a Chiral Phosphoric Acid. AU - Li,Xiao-Qiang, AU - Yang,Hui, AU - Wang,Jiao-Jiao, AU - Gou,Bo-Bo, AU - Chen,Jie, AU - Zhou,Ling, Y1 - 2017/04/03/ PY - 2017/03/06/received PY - 2017/3/9/pubmed PY - 2017/3/9/medline PY - 2017/3/9/entrez KW - aromaticity KW - asymmetric catalysis KW - dearomatization KW - enantioselectivity KW - organocatalysis SP - 5381 EP - 5385 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 23 IS - 22 N2 - An enantioselective arylative dearomatization reaction of β-naphthols with quinone monoimides has been developed for the first time using a chiral phosphoric acid as the catalyst, the desired enantioenriched cyclohexadienones were prepared with excellent yields and enantioselectivities by a domino Michael addition and aromatization process (up to 99 % yield, up to 98 % ee). This process is operationally simple and readily scaled up, as well as a broad substrate scope which includes 1-substituted-2-naphthols with/without 3-substituents. Furthermore, this organocatalytic procedure allows the lowering of catalyst loading to 0.5 mol % without considerable loss in reactivity and enantioselectivity. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/28272764/Asymmetric_Arylative_Dearomatization_of_β_Naphthols_Catalyzed_by_a_Chiral_Phosphoric_Acid_ L2 - https://doi.org/10.1002/chem.201701015 DB - PRIME DP - Unbound Medicine ER -