Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine-Urea Bifunctional Organocatalyst

Tatsuya Orihara, Masaki Kawaguchi, Keisuke Hosoya, Ryosuke Tsutsumi, Masahiro Yamanaka, Minami Odagi, Kazuo Nagasawa

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)15232-15240
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number23
DOIs
Publication statusPublished - 2020 Dec 4
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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