Enantioselective addition of diethylzinc to aldehydes using immobilized chiral BINOL–Ti complex on ordered mesoporous silicas

Pathak, Kavita; Bhatt, Achyut P.; Abdi, Sayed H. R.; Kureshy, Rukhsana I.; Khan, Noor‐ul H.; Ahmad, Irshad; Jasra, Raksh V.

doi:10.1016/j.tetasy.2006.05.017

Cited by 41 publications

(23 citation statements)

References 31 publications

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“…The yield of single triethoxysilane derivatives is higher than that of double derivatives due to the low activity of the second hydroxylmethyl group in compounds 1b and 1d. The chains introduced at different positions of BINOL were -CH 2 O(CH 2 ) 3 -with longer lengths than the organosilane derivative of BINOL reported [37,38] to retain the flexibility of BINOL. The obtained triethoxysilane derivatives of (S)-BINOL were characterized by 1 H NMR, 13 C NMR, 29 Si NMR, FT-IR, ESI-MS and elemental analyses.…”

Section: Preparation and Characterization Of Organosilanementioning

confidence: 91%

“…Various supports such as organic polymers [22][23][24][25][26][27][28][29][30], inorganic materials [31][32][33], dendrimers [34], have been investigated to immobilize BINOLs as metal-centered Lewis acid catalysts in a lot of asymmetric catalytic reactions. Meanwhile, one organosilane derivative of chiral BINOL was post-grafted onto ordered mesoporous silicas MCM-41 [35] and SBA-15 [36] by Abdi and coworkers to catalyze asymmetric nitroaldol reaction [37] and enantioselective addition of diethylzinc to aldehydes [38] centered with different metal ions. However, that organosilane derivative of chiral BINOL could not be purified because of its instability to moisture.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Preparation and Characterization Of Organosilanementioning

confidence: 91%

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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“…9). Also, 10 Asymmetric addition of diethylzinc to aldehydes using heterogeneous catalyst [72] titanium complexes with TADDOLs, BINOLs, and 1,2-disulfonamidocyclohexane ligands showed excellent enantioselectivity [71]. Chiral (S)-BINOL ligand was grafted by us for the first time, on ordered mesoporous silicas-MCM-41 and SBA-15 through covalently bonded linkers (Fig.…”

Section: Asymmetric Addition Of Diethylzinc To Aldehydesmentioning

confidence: 99%

Dimeric & Polymeric Chiral Schiff Base Complexes and Supported BINOL Complexes as Potential Recyclable Catalysts in Asymmetric Kinetic Resolution and C–C Bond Formation Reactions

et al. 2009

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This review is based on dimeric and polymeric chiral Schiff base metal complexes and chiral BINOL supported metal complexes as potential recyclable catalysts for kinetic resolution of racemic and meso epoxide and asymmetric C-C bond formation reactions e.g., asymmetric addition of diethylzinc to aldehydes, enantioselective addition of phenylacetylene to aldehydes, asymmetric nitro-Aldol reactions and asymmetric cyanation reaction.

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“…[7a, 15] Finally, introducing 1 into the nanopores of silica materials and tailoring the pore entrance with diphenyldichlorosilane afforded the heterogeneous catalysts 2-3 according to the reported method.…”

Section: Synthesis and Characterization Of The Catalystmentioning

confidence: 99%

An Ion‐Pair Immobilization Strategy in Rhodium‐Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones

Cheng

Long

et al. 2012

Adv Synth Catal

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A chiral diamine-based homogeneous cationic rhodium catalyst was developed and two heterogeneous cationic rhodium catalysts were obtained via the encapsulation of the homogeneous cationic rhodium catalyst within Me-SBA-15 and Me-SBA-16. All these catalysts presented excellent catalytic activities and high enantioselectivities in ultrasoundpromoted asymmetric transfer hydrogenation of aromatic ketones and represent a successful use of the ion-pair immobilization strategy. More importantly, the encapsulation of the cationic rhodium functionality within Me-SBA-16 had an obvious high recyclability, in which the recycled catalyst could be reused nine times without significantly affecting its enantioselectivity, showing good potential in industrial application.

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Enantioselective addition of diethylzinc to aldehydes using immobilized chiral BINOL–Ti complex on ordered mesoporous silicas

Cited by 41 publications

References 31 publications

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

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

Dimeric & Polymeric Chiral Schiff Base Complexes and Supported BINOL Complexes as Potential Recyclable Catalysts in Asymmetric Kinetic Resolution and C–C Bond Formation Reactions

An Ion‐Pair Immobilization Strategy in Rhodium‐Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones

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