Formation of macrocycles via ring-closing olefin metathesis

被引：115

作者：

Lee, CW ^{[1
]}

Grubbs, RH ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synth, Pasadena, CA 91125 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo0158480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enhanced metathesis activity of 1,3-dimesityl-4,5-dihydroimidazole-2-ylidene ruthenium carbene catalyst 3 significantly increases the feasibility of synthesizing macrocyclic compounds. Catalyst 3 exhibits sufficient activity in RCM to dimerize alpha,beta -unsaturated ester substrates and afford the corresponding head-to-tail (E,E)-dimeric (and trimeric) macrocycles. The dimerization appears to be under thermodynamic control with the product mixture dependent not only on the electronic and steric nature of the substrate but also on concentration.

引用

页码：7155 / 7158

页数：4

共 32 条

[1] Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM) [J].

Arisawa, M ;

Kato, C ;

Kaneko, H ;

Nishida, A ;

Nakagawa, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1873-1876

[2] OXIDATION OF ALPHA,BETA-UNSATURATED ESTERS AND LACTONES WITH SELENIUM DIOXIDE TO GAMMA-OXO OR GAMMA-HYDROXY DERIVATIVES - SYNTHESIS OF (+/-)-A 26771-B AND NORPYRENOPHORIN [J].

BESTMANN, HJ ;

SCHOBERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1985, 24 (09) :791-792

[3] MODEL STUDIES ON THE SYNTHESIS OF MEDIUM-SIZED AND LARGE CARBOCYCLES USING THE IRELAND ENOLATE CLAISEN REARRANGEMENT [J].

CAMERON, AG ;

KNIGHT, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (01) :161-167

[4] Enantioselective synthesis of unsaturated cyclic tertiary ethers by Mo-catalyzed olefin metathesis [J].

Cefalo, DR ;

Kiely, AF ;

Wuchrer, M ;

Jamieson, JY ;

Schrock, RR ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :3139-3140

[5] Synthesis of functionalized olefins by cross and ring-closing metatheses [J].

Chatterjee, AK ;

Morgan, JP ;

Scholl, M ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784

[6] MODELING RING-CHAIN EQUILIBRIA IN RING-OPENING POLYMERIZATION OF CYCLOOLEFINS [J].

CHEN, ZR ;

CLAVERIE, JP ;

GRUBBS, RH ;

KORNFIELD, JA .

MACROMOLECULES, 1995, 28 (07) :2147-2154

[7] Asymmetric total synthesis of (-)-isolaurallene [J].

Crimmins, MT ;

Emmitte, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) :1533-1534

[8] Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands [J].

Fürstner, A ;

Thiel, OR ;

Kindler, N ;

Bartkowska, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7990-7995

[9]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[10] Ruthenium carbene complexes with N,N′-bis(mesityl) imidazol-2-ylidene ligands:: RCM catalysts of extended scope [J].

Fürstner, A ;

Thiel, OR ;

Ackermann, L ;

Schanz, HJ ;

Nolan, SP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2204-2207

← 1 2 3 4 →