Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

Tetsutaro Hattori; Hiroaki Iwato; Koichi Natori; Sotaro Miyano

doi:10.1016/j.tetasy.2004.01.021

Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

Tetsutaro Hattori, Hiroaki Iwato, Koichi Natori, Sotaro Miyano

工学研究科・バイオ工学専攻

研究成果: Article › 査読

8 被引用数 (Scopus)

抄録

A convenient method is presented for the asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1,5-dimenthoxynaphthalene-2,6- dicarboxylate 7 and its regioisomer, dimenthyl 1,4-dimenthoxynaphthalene-2,3- dicarboxylate 10, with 2-methoxynaphthalen-1-ylmagnesium bromide 12 gave enantiomerically and diastereomerically pure dimenthyl 2,2″-dimethoxy-1, 1′:5′,1″-ternaphthalene-2′,6′-dicarboxylate 3 and dimenthyl 2,2″-dimethoxy-1,1′:4′,1″-ternaphthalene- 2′,3′-dicarboxylate 4 in 70% and 63% yields, respectively, after chromatographic purification.

本文言語	English
ページ（範囲）	881-887
ページ数	7
ジャーナル	Tetrahedron Asymmetry
巻	15
号	5
DOI	https://doi.org/10.1016/j.tetasy.2004.01.021
出版ステータス	Published - 2004 3月 8

ASJC Scopus subject areas

触媒
物理化学および理論化学
有機化学
無機化学

文献へのアクセス

10.1016/j.tetasy.2004.01.021

他のファイルとリンク

引用スタイル

@article{4ed429e0766c4bd3b87e87f566efee1b,

title = "Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction",

abstract = "A convenient method is presented for the asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1,5-dimenthoxynaphthalene-2,6- dicarboxylate 7 and its regioisomer, dimenthyl 1,4-dimenthoxynaphthalene-2,3- dicarboxylate 10, with 2-methoxynaphthalen-1-ylmagnesium bromide 12 gave enantiomerically and diastereomerically pure dimenthyl 2,2″-dimethoxy-1, 1′:5′,1″-ternaphthalene-2′,6′-dicarboxylate 3 and dimenthyl 2,2″-dimethoxy-1,1′:4′,1″-ternaphthalene- 2′,3′-dicarboxylate 4 in 70% and 63% yields, respectively, after chromatographic purification.",

author = "Tetsutaro Hattori and Hiroaki Iwato and Koichi Natori and Sotaro Miyano",

note = "Funding Information: We are grateful to Dr. Osamu Yamabe for experimental support. This study was supported in part by a grant from the General Sekiyu Research Promotion Foundation. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2004",

month = mar,

day = "8",

doi = "10.1016/j.tetasy.2004.01.021",

language = "English",

volume = "15",

pages = "881--887",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "5",

}

TY - JOUR

T1 - Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

AU - Hattori, Tetsutaro

AU - Iwato, Hiroaki

AU - Natori, Koichi

AU - Miyano, Sotaro

N1 - Funding Information: We are grateful to Dr. Osamu Yamabe for experimental support. This study was supported in part by a grant from the General Sekiyu Research Promotion Foundation. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2004/3/8

Y1 - 2004/3/8

N2 - A convenient method is presented for the asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1,5-dimenthoxynaphthalene-2,6- dicarboxylate 7 and its regioisomer, dimenthyl 1,4-dimenthoxynaphthalene-2,3- dicarboxylate 10, with 2-methoxynaphthalen-1-ylmagnesium bromide 12 gave enantiomerically and diastereomerically pure dimenthyl 2,2″-dimethoxy-1, 1′:5′,1″-ternaphthalene-2′,6′-dicarboxylate 3 and dimenthyl 2,2″-dimethoxy-1,1′:4′,1″-ternaphthalene- 2′,3′-dicarboxylate 4 in 70% and 63% yields, respectively, after chromatographic purification.

AB - A convenient method is presented for the asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes via the ester-mediated nucleophilic aromatic substitution reaction. Thus, treatment of dimenthyl 1,5-dimenthoxynaphthalene-2,6- dicarboxylate 7 and its regioisomer, dimenthyl 1,4-dimenthoxynaphthalene-2,3- dicarboxylate 10, with 2-methoxynaphthalen-1-ylmagnesium bromide 12 gave enantiomerically and diastereomerically pure dimenthyl 2,2″-dimethoxy-1, 1′:5′,1″-ternaphthalene-2′,6′-dicarboxylate 3 and dimenthyl 2,2″-dimethoxy-1,1′:4′,1″-ternaphthalene- 2′,3′-dicarboxylate 4 in 70% and 63% yields, respectively, after chromatographic purification.

UR - http://www.scopus.com/inward/record.url?scp=1442326284&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1442326284&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2004.01.021

DO - 10.1016/j.tetasy.2004.01.021

M3 - Article

AN - SCOPUS:1442326284

VL - 15

SP - 881

EP - 887

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 5

ER -

Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

抄録

ASJC Scopus subject areas

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル