Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

Douglas Weibel; Vladimir Gevorgyan; Yoshinori Yamamoto

doi:10.1021/jo9717705

Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

Douglas Weibel, Vladimir Gevorgyan, Yoshinori Yamamoto

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Abstract

Several novel crownlike exomethylene paracyclophanes were efficiently synthesized via an intramolecular palladium-catalyzed benzannulation of conjugated bis-enynes. A method for the efficient synthesis of bis-enynes 8, bearing an oligo(oxyethylene) linkage, was developed by utilizing a two-step procedure from commercially available and inexpensive ethylene glycols. A remarkable complete reversal of reactivity of ambident dilithiated nucleophile 4 toward triflate 7 in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was found.

Original language	English (US)
Pages (from-to)	1217-1220
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	63
Issue number	4
DOIs	https://doi.org/10.1021/jo9717705
State	Published - Feb 20 1998
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol",

abstract = "Several novel crownlike exomethylene paracyclophanes were efficiently synthesized via an intramolecular palladium-catalyzed benzannulation of conjugated bis-enynes. A method for the efficient synthesis of bis-enynes 8, bearing an oligo(oxyethylene) linkage, was developed by utilizing a two-step procedure from commercially available and inexpensive ethylene glycols. A remarkable complete reversal of reactivity of ambident dilithiated nucleophile 4 toward triflate 7 in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was found.",

author = "Douglas Weibel and Vladimir Gevorgyan and Yoshinori Yamamoto",

year = "1998",

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doi = "10.1021/jo9717705",

language = "English (US)",

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T1 - Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

AU - Weibel, Douglas

AU - Gevorgyan, Vladimir

AU - Yamamoto, Yoshinori

PY - 1998/2/20

Y1 - 1998/2/20

N2 - Several novel crownlike exomethylene paracyclophanes were efficiently synthesized via an intramolecular palladium-catalyzed benzannulation of conjugated bis-enynes. A method for the efficient synthesis of bis-enynes 8, bearing an oligo(oxyethylene) linkage, was developed by utilizing a two-step procedure from commercially available and inexpensive ethylene glycols. A remarkable complete reversal of reactivity of ambident dilithiated nucleophile 4 toward triflate 7 in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was found.

AB - Several novel crownlike exomethylene paracyclophanes were efficiently synthesized via an intramolecular palladium-catalyzed benzannulation of conjugated bis-enynes. A method for the efficient synthesis of bis-enynes 8, bearing an oligo(oxyethylene) linkage, was developed by utilizing a two-step procedure from commercially available and inexpensive ethylene glycols. A remarkable complete reversal of reactivity of ambident dilithiated nucleophile 4 toward triflate 7 in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was found.

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M3 - Article

AN - SCOPUS:0000247652

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

Abstract

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