Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

Emi Saito; Yuri Matsumoto; Akihiko Nakamura; Yuki Namera; Masahisa Nakada

doi:10.1021/acs.orglett.7b03824

Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

Emi Saito, Yuri Matsumoto, Akihiko Nakamura, Yuki Namera, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.

Original language	English
Pages (from-to)	692-695
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.7b03824
Publication status	Published - 2018 Feb 2

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.",

author = "Emi Saito and Yuri Matsumoto and Akihiko Nakamura and Yuki Namera and Masahisa Nakada",

note = "Funding Information: We acknowledge support of the Materials Characterization Central Laboratory, Waseda University, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle Molecular Strategy from MEXT and a Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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T1 - Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

AU - Saito, Emi

AU - Matsumoto, Yuri

AU - Nakamura, Akihiko

AU - Namera, Yuki

AU - Nakada, Masahisa

N1 - Funding Information: We acknowledge support of the Materials Characterization Central Laboratory, Waseda University, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle Molecular Strategy from MEXT and a Waseda University Grant for Special Research Projects. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/2/2

Y1 - 2018/2/2

N2 - The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.

AB - The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.

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Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

Abstract

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