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Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction.
J Am Chem Soc. 2015 Apr 22; 137(15):4880-3.JA

Abstract

A Rh-catalyzed enantioselective dearomatization of 1-aryl-2-naphthols with internal alkynes via C-H functionalization reaction was achieved. In the presence of a chiral Cp/Rh catalyst and combined oxidants of Cu(OAc)2 and air (oxygen), various highly enantioenriched spirocyclic enones bearing an all-carbon quaternary stereogenic center could be synthesized in 33-98% yields with up to 97:3 er.

Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25853771

Citation

Zheng, Jun, et al. "Asymmetric Dearomatization of Naphthols Via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction." Journal of the American Chemical Society, vol. 137, no. 15, 2015, pp. 4880-3.
Zheng J, Wang SB, Zheng C, et al. Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction. J Am Chem Soc. 2015;137(15):4880-3.
Zheng, J., Wang, S. B., Zheng, C., & You, S. L. (2015). Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction. Journal of the American Chemical Society, 137(15), 4880-3. https://doi.org/10.1021/jacs.5b01707
Zheng J, et al. Asymmetric Dearomatization of Naphthols Via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction. J Am Chem Soc. 2015 Apr 22;137(15):4880-3. PubMed PMID: 25853771.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp²)-H Functionalization/Annulation Reaction. AU - Zheng,Jun, AU - Wang,Shao-Bo, AU - Zheng,Chao, AU - You,Shu-Li, Y1 - 2015/04/10/ PY - 2015/4/9/entrez PY - 2015/4/9/pubmed PY - 2015/4/9/medline SP - 4880 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 137 IS - 15 N2 - A Rh-catalyzed enantioselective dearomatization of 1-aryl-2-naphthols with internal alkynes via C-H functionalization reaction was achieved. In the presence of a chiral Cp/Rh catalyst and combined oxidants of Cu(OAc)2 and air (oxygen), various highly enantioenriched spirocyclic enones bearing an all-carbon quaternary stereogenic center could be synthesized in 33-98% yields with up to 97:3 er. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/25853771/Asymmetric_Dearomatization_of_Naphthols_via_a_Rh_Catalyzed_C_sp²__H_Functionalization/Annulation_Reaction_ DB - PRIME DP - Unbound Medicine ER -
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