Enantioselective ruthenium-catalyzed ring-closing metathesis

被引：407

作者：

Seiders, TJ ^{[1
]}

Ward, DW ^{[1
]}

Grubbs, RH ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol0165692

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS The first enantioselective ruthenium olefin metathesis catalysts have been prepared, and high enantiomeric excesses (up to 90%) are observed in the desymmetrization of achiral trienes. A model consistent with the stereochemical outcome of the reactions is described and suggests side-on olefin binding and reorganization of the halide ligands.

引用

页码：3225 / 3228

页数：4

共 53 条

[1] Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry [J].

Adlhart, C ;

Hinderling, C ;

Baumann, H ;

Chen, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8204-8214

[2]

Aeilts SL, 2001, ANGEW CHEM INT EDIT, V40, P1452, DOI 10.1002/1521-3773(20010417)40:8<1452::AID-ANIE1452>3.0.CO

[3]

2-G

[4] Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex [J].

Alexander, JB ;

La, DS ;

Cefalo, DR ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4041-4042

[5] Cyclopropanation of styrene with ethyl diazoacetate catalyzed by chiral and achiral ruthenium 2,6-bis(imino)pyridyl complexes [J].

Bianchini, C ;

Lee, HM .

ORGANOMETALLICS, 2000, 19 (10) :1833-1840

[6]

Bielawski CW, 2000, ANGEW CHEM INT EDIT, V39, P2903, DOI 10.1002/1521-3773(20000818)39:16<2903::AID-ANIE2903>3.0.CO

[7]

2-Q

[8] STRUCTURE OF BIS(DIMETHYLPHENYLPHOSPHINE)(ETHYLENE)(CARBONYL) DICHLORORUTHENIUM(II), RUCL2(CO)(C2H4)(P(CH3)2(C6H5))2, A 6-COORDINATE D6 COMPLEX CONTAINING ETHYLENE AS A LIGAND [J].

BROWN, LD ;

BARNARD, CFJ ;

DANIELS, JA ;

MAWBY, RJ ;

IBERS, JA .

INORGANIC CHEMISTRY, 1978, 17 (10) :2932-2935

[9] 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

[10] 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

← 1 2 3 4 5 6 →