A ROMP-derived, polymer-supported chiral Schrock catalyst for enantioselective ring-closing olefin metathesis

被引：36

作者：

Kröll, RM ^{[1
]}

Schuler, N ^{[1
]}

Lubbad, S ^{[1
]}

Buchmeiser, MR ^{[1
]}

机构：

[1] Univ Innsbruck, Inst Analyt Chem & Radiochem, A-6020 Innsbruck, Austria

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 21期

关键词：

D O I：

10.1039/b306427a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A permanently polymer-immobilised version of Schrock's molybdenum catalyst was realised via polymerisation of chiral 5,5'-bis(norborn-5-ene-2-ylmethyleneoxymethyl)-3,3'-di-tert-butyl-6,6'-dimethylbiphen-2,2'-diol followed by reaction with the catalyst precursor Mo(N-2,6-i-Pr2C6H3)(CHCMe2Ph)(OSO2CF3)(2)(CH3OCH2CH2OCH3); using this 5-, 6- and 7-membered heterocycles were synthesised via ring-closing metathesis (RCM) from (pro-)chiral substrates in high yields and ee with short reaction times; the catalyst shows low loss of molybdenum during RCM, and was easily separated and recycled.

引用

页码：2742 / 2743

页数：2

共 33 条

[11]

Hultzsch K. C., 2002, ANGEW CHEM, V114, P609

[12] Some recent applications of olefin metathesis in organic synthesis: A review [J].

Ivin, KJ .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 133 (1-2) :1-16

[13] Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts [J].

Jafarpour, L ;

Heck, MP ;

Baylon, C ;

Lee, HM ;

Mioskowski, C ;

Nolan, SP .

ORGANOMETALLICS, 2002, 21 (04) :671-679

[14] Simply assembled and recyclable polymer-supported olefin metathesis catalysts [J].

Jafarpour, L ;

Nolan, SP .

ORGANIC LETTERS, 2000, 2 (25) :4075-4078

[15] Enantioselective synthesis of medium-ring heterocycles, tertiary ethers, and tertiary alcohols by Mo-catalyzed ring-closing metathesis [J].

Kiely, AF ;

Jernelius, JA ;

Schrock, RR ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2868-2869

[16]

Kingsbury J. S., 2001, ANGEW CHEM, V113, P4381

[17] A recyclable Ru-based metathesis catalyst [J].

Kingsbury, JS ;

Harrity, JPA ;

Bonitatebus, PJ ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :791-799

[18] Monolith- and silica-supported carboxylate-based Grubbs-Herrmann-type metathesis catalysts [J].

Krause, JO ;

Lubbad, S ;

Nuyken, O ;

Buchmeiser, MR .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :996-1004

[19]

KRAUSE JO, 2003, IN PRESS CHEM EUR J

[20] Mo-catalyzed asymmetric synthesis of dihydrofurans. Catalytic kinetic resolution and enantioselective desymmetrization through ring-closing metathesis [J].

La, DS ;

Alexander, JB ;

Cefalo, DR ;

Graf, DD ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9720-9721

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