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Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction.
Angew Chem Int Ed Engl. 2015 Dec 01; 54(49):14929-32.AC

Abstract

An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79% yield, 98% ee).

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Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/. slyou@sioc.ac.cn. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin). slyou@sioc.ac.cn.

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

26463712

Citation

Wang, Shou-Guo, et al. "Asymmetric Dearomatization of β-Naphthols Through a Bifunctional-Thiourea-Catalyzed Michael Reaction." Angewandte Chemie (International Ed. in English), vol. 54, no. 49, 2015, pp. 14929-32.

Wang SG, Liu XJ, Zhao QC, et al. Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angew Chem Int Ed Engl. 2015;54(49):14929-32.

Wang, S. G., Liu, X. J., Zhao, Q. C., Zheng, C., Wang, S. B., & You, S. L. (2015). Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angewandte Chemie (International Ed. in English), 54(49), 14929-32. https://doi.org/10.1002/anie.201507998

Wang SG, et al. Asymmetric Dearomatization of β-Naphthols Through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14929-32. PubMed PMID: 26463712.

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

TY - JOUR T1 - Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. AU - Wang,Shou-Guo, AU - Liu,Xi-Jia, AU - Zhao,Qun-Chao, AU - Zheng,Chao, AU - Wang,Shao-Bo, AU - You,Shu-Li, Y1 - 2015/10/14/ PY - 2015/08/26/received PY - 2015/10/15/entrez PY - 2015/10/16/pubmed PY - 2015/10/16/medline KW - Michael reaction KW - asymmetric dearomatization KW - naphthols KW - nitroethylene KW - organocatalysis SP - 14929 EP - 32 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 49 N2 - An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79% yield, 98% ee). SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26463712/Asymmetric_Dearomatization_of_β_Naphthols_through_a_Bifunctional_Thiourea_Catalyzed_Michael_Reaction_ DB - PRIME DP - Unbound Medicine ER -