150338-25-3Relevant academic research and scientific papers
Enantioselective epoxidation of 2-substituted 1,4-naphthoquinones using gem-dihydroperoxides
Bunge, Alexander,Hamann, Hans-Jürgen,McCalmont, Eve,Liebscher, Jürgen
, p. 4629 - 4632 (2009)
New gem-dihydroperoxides were successfully used for DBU-promoted enantioselective epoxidation of 2-substituted 1,4-naphthoquinones. The corresponding 1,4-naphthoquinone epoxides were obtained in yields up to 97% and ee's up to 82%.
Asymmetric Epoxidation of 1,4-Naphthoquinones Catalyzed by Guanidine-Urea Bifunctional Organocatalyst
Kawaguchi, Masaki,Nakano, Katsuhiro,Hosoya, Keisuke,Orihara, Tatsuya,Yamanaka, Masahiro,Odagi, Minami,Nagasawa, Kazuo
supporting information, p. 2811 - 2815 (2018/05/29)
An enantioselective nucleophilic epoxidation of 2-substituted 1,4-naphthoquinones in the presence of a newly developed guanidine-bisurea bifunctional organocatalyst with tert-butyl hydroperoxide (TBHP) as an oxidant is presented. 1,4-Naphthoquinones bearing substituents at C6, C7, and C2 were available for the reaction, and the corresponding epoxides were obtained with 88:12-95:5 er in 71-98% yields. DFT calculations indicated that substituents at C2 and C6 in the terminal Ar group of the catalyst 9k play a key role in controlling the stereochemical outcome.
