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Paper | Special issue | Vol 97, No. 1, 2018, pp.232-252
Published online, 23rd January, 2018
DOI: 10.3987/COM-17-S(T)11
Research on Unique Masked ortho-Benzoquinone Monohemiaminal: Synthesis and Reactions

Yuri Matsumoto, Akihiko Nakamura, Emi Saito, and Masahisa Nakada*

*Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

Synthesis of ortho-benzoquinone monohemiaminals via the oxidative dearomatization/O-cyclization cascades of phenols bearing an ortho substituent derived from an amino alcohol with PIDA is described. The cascade reactions of substrates bearing a chiral substituent were found to proceed in a stereoselective manner. The Diels-Alder reactions of the ortho-benzoquinone monohemiaminals proceed in a highly stereoselective manner. The oxidative dearomatization/O-cyclization cascade affording the ortho-benzoquinone monohemiaminal had never been reported; hence, there is still ample scope for further investigation.