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Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination.
Angew Chem Int Ed Engl. 2015 Feb 16; 54(8):2356-60.AC

Abstract

Catalytic asymmetric aminative dearomatization of 1-substituted 2-naphthols was successfully implemented with electrophilic azodicarboxylates under the catalysis of chiral Sc(III)/pybox complexes. This intermolecular reaction represents a hitherto unknown enantioselective C-N bond-forming process through direct dearomatization of phenolic compounds to generate chiral nitrogen-containing quaternary carbon stereocenters.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nan J
Key Laboratory of Synthetic and Natural Functional Molecular Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069 (China).
Liu J
No affiliation info available
Zheng H
No affiliation info available
Zuo Z
No affiliation info available
Hou L
No affiliation info available
Hu H
No affiliation info available
Wang Y
No affiliation info available
Luan X
No affiliation info available

MeSH

AminationCatalysisMesylatesNaphtholsScandiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25564754

Citation

Nan, Jiang, et al. "Direct Asymmetric Dearomatization of 2-naphthols By Scandium-catalyzed Electrophilic Amination." Angewandte Chemie (International Ed. in English), vol. 54, no. 8, 2015, pp. 2356-60.
Nan J, Liu J, Zheng H, et al. Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination. Angew Chem Int Ed Engl. 2015;54(8):2356-60.
Nan, J., Liu, J., Zheng, H., Zuo, Z., Hou, L., Hu, H., Wang, Y., & Luan, X. (2015). Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination. Angewandte Chemie (International Ed. in English), 54(8), 2356-60. https://doi.org/10.1002/anie.201409565
Nan J, et al. Direct Asymmetric Dearomatization of 2-naphthols By Scandium-catalyzed Electrophilic Amination. Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2356-60. PubMed PMID: 25564754.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination. AU - Nan,Jiang, AU - Liu,Jingjing, AU - Zheng,Huayu, AU - Zuo,Zhijun, AU - Hou,Lei, AU - Hu,Huaiming, AU - Wang,Yaoyu, AU - Luan,Xinjun, Y1 - 2015/01/07/ PY - 2014/09/28/received PY - 2014/11/13/revised PY - 2015/1/8/entrez PY - 2015/1/8/pubmed PY - 2015/10/28/medline KW - amination KW - asymmetric catalysis KW - dearomatization KW - naphthol KW - scandium SP - 2356 EP - 60 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 8 N2 - Catalytic asymmetric aminative dearomatization of 1-substituted 2-naphthols was successfully implemented with electrophilic azodicarboxylates under the catalysis of chiral Sc(III)/pybox complexes. This intermolecular reaction represents a hitherto unknown enantioselective C-N bond-forming process through direct dearomatization of phenolic compounds to generate chiral nitrogen-containing quaternary carbon stereocenters. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25564754/Direct_asymmetric_dearomatization_of_2_naphthols_by_scandium_catalyzed_electrophilic_amination_ DB - PRIME DP - Unbound Medicine ER -