Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents

Nobuyuki Koike; Tetsutaro Hattori; Ayanobu Takeda; Yoshikazu Okaishi; Sotaro Miyano

doi:10.1246/cl.1997.641

Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents

Nobuyuki Koike, Tetsutaro Hattori, Ayanobu Takeda, Yoshikazu Okaishi, Sotaro Miyano

ENG - Biomolecular Engineering

Tohoku University

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

8 Citations (Scopus)

Abstract

Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0°C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(-)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.

Original language	English
Pages (from-to)	641-642
Number of pages	2
Journal	Chemistry Letters
Issue number	7
DOIs	https://doi.org/10.1246/cl.1997.641
Publication status	Published - 1997

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10.1246/cl.1997.641

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title = "Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents",

abstract = "Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0°C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(-)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.",

author = "Nobuyuki Koike and Tetsutaro Hattori and Ayanobu Takeda and Yoshikazu Okaishi and Sotaro Miyano",

year = "1997",

doi = "10.1246/cl.1997.641",

language = "English",

pages = "641--642",

journal = "Chemistry Letters",

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publisher = "The Chemical Society of Japan",

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T1 - Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents

AU - Koike, Nobuyuki

AU - Hattori, Tetsutaro

AU - Takeda, Ayanobu

AU - Okaishi, Yoshikazu

AU - Miyano, Sotaro

PY - 1997

Y1 - 1997

N2 - Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0°C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(-)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.

AB - Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0°C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(-)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.

UR - http://www.scopus.com/inward/record.url?scp=0031525249&partnerID=8YFLogxK

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DO - 10.1246/cl.1997.641

M3 - Article

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SP - 641

EP - 642

JO - Chemistry Letters

JF - Chemistry Letters

IS - 7

ER -

Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents

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