Intramolecular Consecutive Dehydro-Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality

Takanori Shibata; Ayato Sekine; Akihito Mitake; Kyalo Stephen Kanyiva

doi:10.1002/anie.201810174

Intramolecular Consecutive Dehydro-Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality

Takanori Shibata^*, Ayato Sekine, Akihito Mitake, Kyalo Stephen Kanyiva

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.

Original language	English
Pages (from-to)	15862-15865
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	48
DOIs	https://doi.org/10.1002/anie.201810174
Publication status	Published - 2018 Nov 26

Keywords

axial chirality
cycloaddition
enantioselectivity
heterocycles
rhodium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201810174

Cite this

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abstract = "Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.",

keywords = "axial chirality, cycloaddition, enantioselectivity, heterocycles, rhodium",

author = "Takanori Shibata and Ayato Sekine and Akihito Mitake and Kanyiva, {Kyalo Stephen}",

note = "Funding Information: This work was supported by Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support in the [RhCl(cod)]2 supply. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Sekine, Ayato

AU - Mitake, Akihito

AU - Kanyiva, Kyalo Stephen

N1 - Funding Information: This work was supported by Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support in the [RhCl(cod)]2 supply. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/11/26

Y1 - 2018/11/26

N2 - Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.

AB - Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.

KW - axial chirality

KW - cycloaddition

KW - enantioselectivity

KW - heterocycles

KW - rhodium

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Intramolecular Consecutive Dehydro-Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality

Abstract

Keywords

ASJC Scopus subject areas

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