Asymmetric Dearomatization of Naphthols via a Rh-Catalyzed C(sp2)–H Functionalization/Annulation Reaction

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 al...

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Published inJournal of the American Chemical Society Vol. 137; no. 15; pp. 4880 - 4883
Main Authors Zheng, Jun, Wang, Shao-Bo, Zheng, Chao, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.04.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
H BOND ACTIVATION
ENANTIOSELECTIVE DEAROMATIZATION
ALKENES
OXIDATIVE DEAROMATIZATION
ANNULATION
CONSTRUCTION
C-C
PHENOL DEAROMATIZATION
SPIROLACTONIZATION
CRAFTS ALLYLIC ALKYLATION
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Summary: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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b01707