Asymmetric addition of diethylzinc to benzaldehyde catalyzed by silica-immobilized titanium(IV) complexes of N-sulfonylated amino alcohols

Huang, Lu-Ning; Hui, Xin‐Ping; Xu, Peng‐Fei

doi:10.1016/j.molcata.2006.05.048

Cited by 9 publications

(2 citation statements)

References 27 publications

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“…The catalyst 108 ( Fig. 1.47 ) showed an impressive recycling ability, since it was reused nine times without any signifi cant decrease of reactivity and enantioselectivity [209] . Heterogeneous supports furnished a more robust catalyst than those prepared for homogeneous catalysis, in which soluble polystyrene polymers [210] and dentritic [211,212] structures were examined as supports.…”

Section: Chiral Aminoalcoholsmentioning

confidence: 99%

Recyclable Stereoselective Catalysts

Monteiro¹,

Trindade²,

Góis

et al. 2011

Catalytic Methods in Asymmetric Synthesis

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Section: Chiral Aminoalcoholsmentioning

confidence: 99%

Recyclable Stereoselective Catalysts

Monteiro¹,

Trindade²,

Góis

et al. 2011

Catalytic Methods in Asymmetric Synthesis

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“…Generally, pre-grafting method of chiral ligands on mesoporous silicas and coordination with mental ions afterwards [7] has been predominantly applied. However, it is inevitable that some metal ions could not coordinate with the chiral ligands pre-grafted on the mesoporous silicas [8] since they react with Si-OH groups of the supports which would influence the activity and enantioselectivity of the catalytic reactions at the final stage [9,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Catalytic Properties of Chiral BINOL Functionalized Mesoporous Silicas for Enantioselective Morita-Baylis-Hillman Reaction

et al. 2008

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Several Chiral BINOL functionalized mesoporous silicas were prepared by post grafting of organosilane derivatives of (S)-BINOL (1,1 0 -bi-2-naphthol) on SBA-15 and characterized by 13 C CP/MAS NMR, FT-IR, UV-visible absorption spectra, elemental analysis, powder XRD, nitrogen adsorption-desorption isotherms and TEM techniques. Their catalytic properties were demonstrated in enantioselective Morita-Baylis-Hillman reaction of 3-phenylpropanal and cyclohexenone. Among them, 3BSBA-15 linked through the 3 position of BINOL exhibit higher enantioselectivity (26% e.e.) and yield (88%) which are similar to the homogeneous catalyst (S)-BINOL (27% e.e. and 92% yield) as Brønsted acids catalyst, while complex of 3BSBA-15 and calcium 3BSBA-15-Ca show lower enantioselectivity (21% e.e.) than its homogeneous complex (S)-BINOL-Ca (32% e.e.) as ligand catalyst. 3BSBA-15 and 3BSBA-15-Ca can be reused with no significant decrease in enantioselectivity and yield.

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