Exploitation of perfluorophenyl-phenyl interactions for achieving difficult macrocyclizations by using ring-closing metathesis

被引：49

作者：

El-Azizi, Y ^{[1
]}

Schmitzer, A ^{[1
]}

Collins, SK ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 06期

关键词：

alkene metathesis; cyclophanes; macrocyclization; perfluoroarenes; quadrupolar interactions;

D O I：

10.1002/anie.200503112

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Correct orientation: Macrocyclic paracyclophanes of multiple ring sizes and diverse functionality are prepared byolefin metathesis (see scheme for an example), through the exploitation of solution-phase quadrupolar interactions between the core arene and pendant pentafluoroarene units. This approach reverses the tendency for dimeric products to be formed during macrocyclizations. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：968 / 973

页数：6

共 37 条

[11] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[12] Longithorones, unique prenylated para- and metacyclophane type quinones from the tunicate Aplidium longithorax [J].

Fu, X ;

Hossain, MB ;

Schmitz, FJ ;

vanderHelm, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3810-3819

[13] Exploiting the reversibility of olefin metathesis.: Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin [J].

Fürstner, A ;

Thiel, OR ;

Ackermann, L .

ORGANIC LETTERS, 2001, 3 (03) :449-451

[14] Olefin metathesis [J].

Grubbs, RH .

TETRAHEDRON, 2004, 60 (34) :7117-7140

[15] Ring closing enyne metathesis: Control over mode selectivity and stereoselectivity [J].

Hansen, EC ;

Lee, DS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15074-15080

[16] N-alkylation of anilines, carboxamides and several nitrogen heterocycles using CsF-celite/alkyl halides/CH3CN combination [J].

Hayat, S ;

Atta-ur-Rahman ;

Choudhary, MI ;

Khan, KM ;

Schumann, W ;

Bayer, E .

TETRAHEDRON, 2001, 57 (50) :9951-9957

[17] Relay ring-closing metathesis (RRCM): A strategy for directing metal movement throughout olefin metathesis sequences [J].

Hoye, TR ;

Jeffrey, CS ;

Tennakoon, MA ;

Wang, JZ ;

Zhao, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10210-10211

[18] π shielding in organic synthesis [J].

Jones, GB .

TETRAHEDRON, 2001, 57 (38) :7999-8016

[19] Cyclization of polyenes.: 58.: Synthesis of longithorone B, a sixteen-membered farnesylated p-benzoquinone [J].

Kato, T ;

Nagae, K ;

Hoshikawa, M .

TETRAHEDRON LETTERS, 1999, 40 (10) :1941-1944

[20] Magic ring rotaxanes by olefin metathesis [J].

Kilbinger, AFM ;

Cantrill, SJ ;

Waltman, AW ;

Day, MW ;

Grubbs, RH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3281-3285

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