A New Class of Chiral Lewis Acid Catalysts for Highly Enantioselective Hetero-Diels-Alder Reactions:  Exceptionally High Turnover Numbers from Dirhodium(II) Carboxamidates

Doyle, Michael P.; Phillips, Iain M.; Hu, Wenhao

doi:10.1021/ja015692l

Cited by 105 publications

(51 citation statements)

References 13 publications

(16 reference statements)

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“…Rhodium(II) carboxylates of type Rh 2 (O 2 CR) 4 L 2 ,inwhich Lrepresents aLewis base and Ranorganic group, have been attracting much attention in recent years due to their potential applications as catalysts [1,2], antitumor agents [3,4] and building blocks for supramolecular arrays [5,6]. Rhodium(II) carboxylates readily form adducts in which the axial sites are occupied by donor solvents or ligands, which has led to the isolation of alarge number of adducts [6,7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of tetrakis(acetato)bis(4-pyridinemethanol)dirhodium, Rh2(C2H3O2)4(C6H7NO)2

Ye¹,

Chen²,

Xie³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of tetrakis(acetato)bis(4-pyridinemethanol)dirhodium, Rh2(C2H3O2)4(C6H7NO)2

Ye¹,

Chen²,

Xie³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…A considerable amount of work [1][2][3][4][5][6][7][8] has now been reported on the chemical and structural properties of rhodium(II) carboxylates with general formula Rh 2 (OOCR) 4 L 2 , in which L represents a Lewis base and R an organic group. Rhodium(II) carboxylates readily form adducts in which the axial sites are occupied by donor solvents or ligands, leading to the isolation of a large number of adducts.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of tetrakis(µ2-formiato-κ2O:O')bis(4-methylpyridine-κN) dirhodium(II) (Rh–Rh), C16H18N2O8Rh2

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialRh 2 (O 2 CH) 4 (H 2 O) 2 (10 mg, 0.024 mmol) was dissolved in 5ml of distilled water. Slow vapor diffusion of 4-methylpyridine into the solution in two weeks yielded pink prism crystals suitable for crystallographic analysis. Experimental detailsThe H atoms of the methyl were positioned geometrically (d(C-H) = 0.96 Å), and refined as riding with U iso (H) = 1.5 U eq (C). The other H atoms were positioned geometrically (d(C-H) = 0.93 Å), and refined as riding with U iso (H) = 1.2 U eq (C). (5) Å), and almost equivalent to that in Rh 2 (OOCCH 3 ) 4 (4-pyridinemethanol) 2 (2.4030(7) Å) [9][10][11]. The range of Rh-O distances ranges from 2.029(4) to 2.045(4) Å and the Rh-N distance is 2.241(4) Å, agreeing well with the data of rhodium(II) carboxylates [1,[8][9][10][11]. The Rh-Rh-O angles have a mean value of 89.9(7)°, individual angles being in the range 89.4(2) to 90.4(2)°. The four carboxylate oxygen atoms around Rh atom define a square plane from which the Rh atom is displaced by 0.0754(4) Å, toward the axial nitrogen atoms. The axial Rh-Rh-N angle is close to linear with a value of 179.26(9)°. The pyridine rings are planar with no deviations greater than 0.010 Å. The pyridine rings of neighbouring complexes are parallel to each other with a distance of 3.563 Å . Discussion

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“…Their remarkable selectivity has reached a stage where they can function as a powerful tool in building up value added molecules with complex structures [7,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

et al. 2018

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A New Class of Chiral Lewis Acid Catalysts for Highly Enantioselective Hetero-Diels-Alder Reactions: Exceptionally High Turnover Numbers from Dirhodium(II) Carboxamidates

Cited by 105 publications

References 13 publications

Crystal structure of tetrakis(acetato)bis(4-pyridinemethanol)dirhodium, Rh2(C2H3O2)4(C6H7NO)2

Crystal structure of tetrakis(acetato)bis(4-pyridinemethanol)dirhodium, Rh2(C2H3O2)4(C6H7NO)2

Crystal structure of tetrakis(µ2-formiato-κ2O:O')bis(4-methylpyridine-κN) dirhodium(II) (Rh–Rh), C16H18N2O8Rh2

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

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