Asymmetric catalysts for stereocontrolled olefin metathesis reactions

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

“…This review will present recent advancements (since 2010) in stereoselective OM employing ruthenium catalysts which directly convey stereochemical control on the products for synthetic applications. Also, much progress has recently been made in the use of stereoselective molybdenum and tungsten metathesis catalysts [16,17,[21][22][23]; however, this review will focus on ruthenium-based metathesis catalysts.…”

“…Early stereoselective OM research focused on the desymmetrization of achiral olefins to provide chiral molecules through the alteration of the ligand scaffold [11,16,17]. As understanding for the stereochemical arrangement stereoselective OM research focused on the desymmetrization of achiral olefins to provide chiral molecules through the alteration of the ligand scaffold [11,16,17].…”

“…Early stereoselective OM research focused on the desymmetrization of achiral olefins to provide chiral molecules through the alteration of the ligand scaffold [11,16,17]. As understanding for the stereochemical arrangement stereoselective OM research focused on the desymmetrization of achiral olefins to provide chiral molecules through the alteration of the ligand scaffold [11,16,17]. As understanding for the stereochemical arrangement of the metallacycle intermediate progressed, further variations were made in continual pursuit of one of the unmet challenges in OM: kinetic Z-selectivity [18][19][20].…”

Enantiopure C1-symmetric N-Heterocyclic Carbene Ligands from Desymmetrized meso-1,2-Diphenylethylenediamine: Application in Ruthenium-Catalyzed Olefin Metathesis

“…Among them, asymmetric transformations mediated by metal catalysts bearing NHCs with chiral architectures have attracted increasing interest, and intensive research efforts have permitted the obtainment of highly stereoselective catalysts [5,6]. The employment of stable, easy-handling chiral NHC Ru-based catalysts has resulted in significant advancements in asymmetric olefin metathesis, a powerful methodology for carbon-carbon bond formation leading to enantioenriched molecules [7][8][9][10][11]. A number of highly enantioselective catalysts bearing C 2 -and C 1 -symmetric NHC ligands derived from chiral 1,2-diamines were reported by Grubbs [12][13][14] and Collins [15][16][17][18] (Figure 1).…”

Synthesis and Reactivity of a Pentacoordinated Thiolate-Based Imido-Alkylidene W(VI) Complexes

“…For these reasons, the development of homogeneous and heterogeneous metathesis catalysts still attracts major attention [3,4]. Well-defined alkylidenes in high oxidation states, with electron-withdrawing ligands were identified as highly efficient metathesis catalysts [5][6][7], following the proposal by Chauvin that they were key intermediates [8,9]. Recent progress in the understanding of the structure-activity relationship, involving surface chemistry [10][11][12][13] combined with computational studies [14][15][16][17], has highlighted trends for a more rational design of alkene metathesis catalysts and shown in particular that dissymmetry at the metal center can bring about high activity.…”