TY - JOUR
T1 - Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine-Urea Bifunctional Organocatalyst
AU - Orihara, Tatsuya
AU - Kawaguchi, Masaki
AU - Hosoya, Keisuke
AU - Tsutsumi, Ryosuke
AU - Yamanaka, Masahiro
AU - Odagi, Minami
AU - Nagasawa, Kazuo
N1 - Funding Information:
The authors thank Professor Dr. Keiichi Noguchi (Tokyo University of Agriculture and Technology) for his support in the X-ray crystallographic analysis. This research was funded by the Grants-in-Aid for Scientific Research on Innovative Areas “Middle Molecular Strategy” (18H04387 to K.N.), “Hybrid Catalysis” (20H04828 to M.Y.), Grants-in-Aid for Scientific Research (B) (17H03052 to K.N.), and the A3-foresight program from the Japan Society for the Promotion of Science (JSPS). T.O. thanks DAICEL Co. Ltd. for the financial support. K.H. was supported by the Grants-in-Aid for a JSPS fellowship (19 J13325). M.O. is grateful for JSPS KAKENHI grant numbers 18 K14210 and 20 K05488. This work was inspired by the international and interdisciplinary environment of the JSPS Asian CORE Program of ACBI (Asian Chemical Biology Initiative).
Publisher Copyright:
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PY - 2020/12/4
Y1 - 2020/12/4
N2 - An organocatalytic enantioselective epoxidation of 2,3-disubstituted naphthoquinones with tert-butyl hydroperoxide as an oxidant was developed using a guanidine-urea bifunctional catalyst lacking C2 symmetry, which was designed based upon the insights obtained from the DFT calculation model for our previous C2 symmetric catalyst. The present organocatalytic reaction provides access to a variety of optically active naphthoquinone epoxides bearing aryl and methyl substituents at C2 and C3 in high yields with high enantioselectivities (up to 97:3 er).
AB - An organocatalytic enantioselective epoxidation of 2,3-disubstituted naphthoquinones with tert-butyl hydroperoxide as an oxidant was developed using a guanidine-urea bifunctional catalyst lacking C2 symmetry, which was designed based upon the insights obtained from the DFT calculation model for our previous C2 symmetric catalyst. The present organocatalytic reaction provides access to a variety of optically active naphthoquinone epoxides bearing aryl and methyl substituents at C2 and C3 in high yields with high enantioselectivities (up to 97:3 er).
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U2 - 10.1021/acs.joc.0c02084
DO - 10.1021/acs.joc.0c02084
M3 - Article
AN - SCOPUS:85096868516
SN - 0022-3263
VL - 85
SP - 15232
EP - 15240
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -