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Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.
Chem Sci. 2017 Sep 01; 8(9):6645-6649.CS

Abstract

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.

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Authors+Show Affiliations

Zhang Y
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
Liao Y
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
Liu X
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
Xu X
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
Lin L
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
Feng X
Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28989691

Citation

Zhang, Yu, et al. "Catalytic Asymmetric Hydroxylative Dearomatization of 2-naphthols: Synthesis of Lacinilene Derivatives." Chemical Science, vol. 8, no. 9, 2017, pp. 6645-6649.
Zhang Y, Liao Y, Liu X, et al. Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives. Chem Sci. 2017;8(9):6645-6649.
Zhang, Y., Liao, Y., Liu, X., Xu, X., Lin, L., & Feng, X. (2017). Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives. Chemical Science, 8(9), 6645-6649. https://doi.org/10.1039/c7sc02809a
Zhang Y, et al. Catalytic Asymmetric Hydroxylative Dearomatization of 2-naphthols: Synthesis of Lacinilene Derivatives. Chem Sci. 2017 Sep 1;8(9):6645-6649. PubMed PMID: 28989691.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives. AU - Zhang,Yu, AU - Liao,Yuting, AU - Liu,Xiaohua, AU - Xu,Xi, AU - Lin,Lili, AU - Feng,Xiaoming, Y1 - 2017/07/24/ PY - 2017/06/24/received PY - 2017/07/20/accepted PY - 2017/10/10/entrez PY - 2017/10/11/pubmed PY - 2017/10/11/medline SP - 6645 EP - 6649 JF - Chemical science JO - Chem Sci VL - 8 IS - 9 N2 - An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed. SN - 2041-6520 UR - https://www.unboundmedicine.com/medline/citation/28989691/Catalytic_asymmetric_hydroxylative_dearomatization_of_2_naphthols:_synthesis_of_lacinilene_derivatives_ DB - PRIME DP - Unbound Medicine ER -
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