, volume 84 , issue 21 , pages 14248-14257

Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex

ryo Sato ¹

Takuya Tosaka ¹

Hyuma Masu ²

Takayoshi Arai ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Soft Molecular Activation Research Center (SMARC), Chiba Iodine Research Innovation Center (CIRIC), and Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan |

Center for Analytical Instrumentation, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan |

Publication type: Journal Article

Publication date: 2019-09-25

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b02006

Copy DOI

PubMed ID: 31553607

Organic Chemistry

Abstract

A chiral tosyl-substituted bis(imidazolidine)pyridine Ts-PyBidine-nickel complex was an efficient catalyst for Friedel-Crafts reaction of indoles with methylene indolinones to give bisindolylmethane compounds having differently oxidized indole units with high enantioselectivities. Alkylation of the products proceeded smoothly in a highly diastereoselective manner, providing an all-carbon quaternary carbon center without significant loss of enantiomeric excess.

Found

1 citation

Zaharani Lia

34 publications, 174 citations

h-index: 8

University of Malaya

Top-30

Journals

	1 2 3
Journal of Organic Chemistry	Journal of Organic Chemistry, 3, 16.67% Journal of Organic Chemistry 3 publications, 16.67%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 2, 11.11% Organic and Biomolecular Chemistry 2 publications, 11.11%
Molecules	Molecules, 1, 5.56% Molecules 1 publication, 5.56%
Journal of Molecular Structure	Journal of Molecular Structure, 1, 5.56% Journal of Molecular Structure 1 publication, 5.56%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 5.56% Asian Journal of Organic Chemistry 1 publication, 5.56%
Dalton Transactions	Dalton Transactions, 1, 5.56% Dalton Transactions 1 publication, 5.56%
ACS Omega	ACS Omega, 1, 5.56% ACS Omega 1 publication, 5.56%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 1, 5.56% Organic Chemistry Frontiers 1 publication, 5.56%
Molecular Catalysis	Molecular Catalysis, 1, 5.56% Molecular Catalysis 1 publication, 5.56%
Synthetic Communications	Synthetic Communications, 1, 5.56% Synthetic Communications 1 publication, 5.56%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 5.56% Topics in Current Chemistry 1 publication, 5.56%
Synthesis	Synthesis, 1, 5.56% Synthesis 1 publication, 5.56%
Mendeleev Communications	Mendeleev Communications, 1, 5.56% Mendeleev Communications 1 publication, 5.56%
Chinese Journal of Chemistry	Chinese Journal of Chemistry, 1, 5.56% Chinese Journal of Chemistry 1 publication, 5.56%
	1 2 3

Publishers

	1 2 3 4
American Chemical Society (ACS)	American Chemical Society (ACS), 4, 22.22% American Chemical Society (ACS) 4 publications, 22.22%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 22.22% Royal Society of Chemistry (RSC) 4 publications, 22.22%
Elsevier	Elsevier, 3, 16.67% Elsevier 3 publications, 16.67%
Wiley	Wiley, 2, 11.11% Wiley 2 publications, 11.11%
MDPI	MDPI, 1, 5.56% MDPI 1 publication, 5.56%
Taylor & Francis	Taylor & Francis, 1, 5.56% Taylor & Francis 1 publication, 5.56%
Springer Nature	Springer Nature, 1, 5.56% Springer Nature 1 publication, 5.56%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 5.56% Georg Thieme Verlag KG 1 publication, 5.56%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 1, 5.56% OOO Zhurnal "Mendeleevskie Soobshcheniya" 1 publication, 5.56%
	1 2 3 4

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Sato R. et al. Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 14248-14257.

GOST all authors (up to 50) Copy

Sato R., Tosaka T., Masu H., Arai T. Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 14248-14257.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.9b02006

UR - https://doi.org/10.1021/acs.joc.9b02006

TI - Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex

T2 - Journal of Organic Chemistry

AU - Sato, ryo

AU - Tosaka, Takuya

AU - Masu, Hyuma

AU - Arai, Takayoshi

PY - 2019

DA - 2019/09/25

PB - American Chemical Society (ACS)

SP - 14248-14257

IS - 21

VL - 84

PMID - 31553607

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Sato,

author = {ryo Sato and Takuya Tosaka and Hyuma Masu and Takayoshi Arai},

title = {Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {sep},

url = {https://doi.org/10.1021/acs.joc.9b02006},

number = {21},

pages = {14248--14257},

doi = {10.1021/acs.joc.9b02006}

}

MLA

Cite this

MLA Copy

Sato, ryo, et al. “Catalytic Asymmetric Synthesis of Chiral Bis(indolyl)methanes Using a Ts-PyBidine–Nickel Complex.” Journal of Organic Chemistry, vol. 84, no. 21, Sep. 2019, pp. 14248-14257. https://doi.org/10.1021/acs.joc.9b02006.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)