Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition

Akihito Mitake; Toru Fusamae; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1002/ejoc.201701532

Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition

Akihito Mitake, Toru Fusamae, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.

Original language	English
Pages (from-to)	7266-7270
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	48
DOIs	https://doi.org/10.1002/ejoc.201701532
Publication status	Published - 2017 Dec 29

Keywords

Alkynes
Axial chirality
Cycloaddition
Enantioselectivity
Heterocycles
Rhodium

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201701532

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title = "Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition",

abstract = "The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.",

keywords = "Alkynes, Axial chirality, Cycloaddition, Enantioselectivity, Heterocycles, Rhodium",

author = "Akihito Mitake and Toru Fusamae and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: This work was supported by JST, ACT-C, Japan and a Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support through the supply of [Rh(cod)Cl]2. Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ejoc.201701532",

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journal = "European Journal of Organic Chemistry",

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AU - Mitake, Akihito

AU - Fusamae, Toru

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by JST, ACT-C, Japan and a Waseda University Grant for Special Research Projects. We are grateful to Umicore for generous support through the supply of [Rh(cod)Cl]2. Publisher Copyright: © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/12/29

Y1 - 2017/12/29

N2 - The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.

AB - The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.

KW - Alkynes

KW - Axial chirality

KW - Cycloaddition

KW - Enantioselectivity

KW - Heterocycles

KW - Rhodium

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DO - 10.1002/ejoc.201701532

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VL - 2017

SP - 7266

EP - 7270

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 48

ER -

Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition

Abstract

Keywords

ASJC Scopus subject areas

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