Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes

Belokoń, Yuri N.; Ikonnikov, N. S.; Moscalenko, Margarita A.; North, Michael; Orlova, S. A.; Tararov, Vitali I.; Yashkina, L. V.

doi:10.1016/0957-4166(96)00083-3

Cited by 87 publications

(45 citation statements)

References 9 publications

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“…[40] 3.3.2. Aldol Reactions Kobayashi and Mukaiyama et al have shown that asymmetric aldol reactions of achiral silylenol ethers can be performed with excellent stereochemical control by the combined use of tin(ii) triflate, dibutyltin diacetate, and a chiral 1,2-diamine (Scheme 14).…”

Section: Alkylation Of Aldehydesmentioning

confidence: 98%

See 1 more Smart Citation

The Chemistry of Vicinal Diamines

Lucet

Gall

Mioskowski³

1998

Angewandte Chemie International Edition

946

414

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Section: Alkylation Of Aldehydesmentioning

confidence: 98%

“…Helmchen et al [23a] described the homoaldol addition of the titanium compound obtained from N-alkylurea 39 with aldehydes or ketones. This reaction afforded alcohols 39' ' (de 88 ± 96 %, de b 98 % after recrystallization), which were then converted to g-lactones 40. Cardillo et al…”

Section: Vicinal Diamines and Their Derivatives As Chiral Auxiliariesmentioning

confidence: 99%

The Chemistry of Vicinal Diamines

Lucet

Gall

Mioskowski³

1998

Angewandte Chemie International Edition

946

414

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show abstract

“…More recently, North and co-workers have reported the asymmetric version of this reaction using chiral dichlorotitanium-and vanadyl-salen complexes. [175][176][177][178] A mesoporous hybrid organosilica containing a disilyl derivative of a vanadyl-salen complex has been synthesized using as silicon sources tetraethyl orthosilicate and a disilyl derivative of a vanadyl-salen complex. [179] The solid containing the vanadyl-salen complex results when both sources of silicon co-condense in the presence of cetyltrimethylammonium as structure-directing agent.…”

Section: Silica-bound Heterogeneous Catalysts For Enantioselective Cymentioning

confidence: 99%

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

2006

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Very frequently the most costly components in a chemical reaction are not the starting materials or the reaction products, but the catalyst. In addition to the advantages from the economic point of view, recovery and reuse of the catalyst is equally important in order to avoid wastes, so improving the greenness of the process. There is a current tendency to transform homogeneous into heterogeneous catalysis, that will even be accelerated in the near future. Starting from a successful homogeneous catalyst, one general methodology allowing its recovery and reuse is to immobilize a suitable derivative of the active catalyst on an insoluble solid support. When the catalyst does not deactivate and is sufficiently stable under the reaction conditions, the ultimate immobilization methodology is to attach covalently the catalytically active species to the support. In this contribution, after introducing some general principles describing the fundamentals of the covalent anchoring, the emphasis is placed more on giving an overview of the most important types of covalently anchored catalysts, including Brçnsted and Lewis acids, covalently anchored bases and hydrogenation complexes. Hot topics such as silica-bound organocatalysts and the application of periodic mesoporous organosilicas as heterogeneous catalysts is also covered.

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“…Most of the known Salen ligands (see a typical salicylethylenediamine ligand 1 in Scheme 1) are usually synthesized by condensation of salicylaldehyde derivatives with diamines, and their complexes with transition metals can catalyze several kinds of organic reactions, such as epoxidation of non-functionalized alkenes [1,2], oxidation [3,4], cyclopropanation [5], trimethylsilylcyanation of aldehydes [6,7], Diels-Alder reactions [8,9], and so on. In particular, the typical Mn(III) complexes as high-efficient epoxidative catalysts have been extensively reported [10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Novel homogeneous Salen Mn(III) catalysts synthesized from dialdehyde or diketone with o-aminophenol for catalyzing epoxidation of alkenes

Xiong

Zhong

et al. 2007

Catal Lett

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A series of novel non-salicylaldehyde based Salen ligands have been synthesized from the condensation of dialdehyde or diketone with o-aminophenol and the corresponding manganese(III) complexes prepared by further coordination of them with Mn(OAc) 2 Á 2H 2 O . FT-IR, UV-Vis spectra, chemical analysis and the structure optimized by Hartree-Fork/3-21G+ all indicated that the qualities of these novel Mn complexes were relative to their molecular structures. More specifically, glyoxal based Mn complex 2c, which was similar to the traditional Mn(III)-salicylethylenediamine, had a short carbon chain and non geometrical constraint of the aliphatic bridge in the two o-aminophenol, and its quality was the best when compared to glutaraldehyde, 2,4-pentanedione and 1,3-cyclohexanedione based Salen Mn(III) complexes (3c, 4c and 5c). And it was also the excellent catalyst for the epoxidations of several non-functionalized alkenes with molecular oxygen/sacrificial-isobutyaldehyde, PhI(OAc) 2 or H 2 O 2 as oxidant.

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Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes

Cited by 87 publications

References 9 publications

The Chemistry of Vicinal Diamines

The Chemistry of Vicinal Diamines

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

Novel homogeneous Salen Mn(III) catalysts synthesized from dialdehyde or diketone with o-aminophenol for catalyzing epoxidation of alkenes

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