Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

Shota Nagasawa; Yusuke Sasano; Yoshiharu Iwabuchi

doi:10.1002/anie.201607752

Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

28 Citations (Scopus)

Abstract

Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.

Original language	English
Pages (from-to)	13189-13194
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	42
DOIs	https://doi.org/10.1002/anie.201607752
Publication status	Published - 2016 Oct 10

Keywords

alkenes
dehydrogenation
ene reaction
regioselectivity
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201607752

Cite this

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title = "Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts",

abstract = "Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.",

keywords = "alkenes, dehydrogenation, ene reaction, regioselectivity, synthetic methods",

author = "Shota Nagasawa and Yusuke Sasano and Yoshiharu Iwabuchi",

note = "Funding Information: This research was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysis” (No. 23105011 to Y.I.) from MEXT, Japan and by a Grant-in-Aid for JSPS fellows (No. 266364 to S.N.). We thank Steven W. M. Crossley (The Scripps Research Institute) for useful discussions. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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month = oct,

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doi = "10.1002/anie.201607752",

language = "English",

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T1 - Synthesis of 1,3-Cycloalkadienes from Cycloalkenes

T2 - Unprecedented Reactivity of Oxoammonium Salts

AU - Nagasawa, Shota

AU - Sasano, Yusuke

AU - Iwabuchi, Yoshiharu

N1 - Funding Information: This research was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysis” (No. 23105011 to Y.I.) from MEXT, Japan and by a Grant-in-Aid for JSPS fellows (No. 266364 to S.N.). We thank Steven W. M. Crossley (The Scripps Research Institute) for useful discussions. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/10/10

Y1 - 2016/10/10

N2 - Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.

AB - Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.

KW - alkenes

KW - dehydrogenation

KW - ene reaction

KW - regioselectivity

KW - synthetic methods

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DO - 10.1002/anie.201607752

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JO - Angewandte Chemie - International Edition

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ER -

Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

Abstract

Keywords

ASJC Scopus subject areas

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