Synthesis of Functionalized Olefins by Cross and Ring-Closing Metatheses

Ruthenium vinyl carbene intermediates in enyne metathesis

“…The second vinyl carbene complex 6 features the N-heterocyclic carbene supporting ligand, which is typical of the 'second generation' Grubbs carbenes. [7,8] When the latter two stable ruthenium vinyl carbene complexes are employed as initiators, they produce alkylidene intermediates. The derived ruthenium alkylidenes are involved in catalysis.…”

Tandem Catalysis: The Sequential Mediation of Olefin Metathesis, Hydrogenation, and Hydrogen Transfer with Single-Component Ru Complexes

“…Complexes (PCy 3 ) 2 Cl 2 Ru=CHPh (1) 1 and (H 2 IMes)(PCy 3 )Cl 2 Ru=CHPh (2) 2 and substrates 1,6-heptadien-4-one (6), 3 1,8-nonadien-5-one (12), 4 2-allyl-2-(2-methyl-allyl)-malonic acid diethyl ester (15), 5 1,4-bis-allyloxy-but-2-yne (21), 4 2-methyl-acrylic acid but-3-enyl ester (24), 6 N-allyl-N-isopropyl-acrylamide (27), 7 and undec-10-enoic acid but-3-enyl ester (30) 8 were prepared as previously reported.…”

“…Substrates 4,4-dicarbethoxycyclopentene (4), 2 cyclopent-3-enone (7), cyclopent-3-enol (10), 2 cyclohept-4-enone (13), 4,4-dicarbethoxy-1-methylcyclopentene (16), 5 2,5,2',5'-tetrahydro- [3,3']bifuranyl (22), 9 3-methyl-5,6-dihydro-pyran-2-one (25), 6 1-isopropyl-1,5-dihydro-pyrrol-2-one (28), 10 oxacyclotetradec-11-en-2-one (31), 8 acetic acid 4-phenyl-but-2-enyl ester (33), 11 acetic acid 7-oxo-oct-5-enyl ester (35), 6 4-phenyl-but-3-en-2-one (37), 12 and 3-(4-chloro-phenyl)-acrylic acid methyl ester S2 (39) 12 are known metathesis products. 1 H (300 MHz) and 13 D were determined on a Jasco Model P-1010 polarimeter in methanol and are given in 10 -1 deg cm 2 g -1 .…”

Synthesis of substituted cycloalkene-1,1-dicarboxylates via olefin metathesis in water

“…Metathesis reactions in water have gained increasing interest in the last years, [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] and provide a range of advantages such as a high potential for the development of sustainable syntheses. Our interest in this field also resulted from the goal to combine metathesis as a metal-catalyzed reaction with enzymatic reactions, which typically require water as the solvent of choice, towards one-pot processes running in the same (aqueous) solvent.…”