An improved and general synthesis of monomers for incorporating trityl linker groups into polystyrene synthesis supports

Choi, Matthew Kwok Wai; Toy, Patrick H.

doi:10.1016/j.tet.2004.01.027

Cited by 17 publications

(11 citation statements)

References 48 publications

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“…For these reactions, it was also found that resins with less than maximum loading levels afforded the best results in terms of product yield and reaction time. We, therefore, chose to examine if our previously reported J anda J el-PPh 3 polymers, ,, which have loading levels of 0.5, 1.5, and 3.2 mmol PPh 3 gm -1 ( 1a − c , respectively), were effective catalysts and if they exhibit such loading-dependent catalytic efficiency in aza-Baylis−Hillman reactions…”

mentioning

confidence: 99%

Polystyrene-Supported Phosphine-Catalyzed aza-Baylis−Hillman Reactions and the Relationship between Resin Loading Level and Catalyst Efficiency

Zhao

Shi

et al. 2004

J. Comb. Chem.

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mentioning

confidence: 99%

Polystyrene-Supported Phosphine-Catalyzed aza-Baylis−Hillman Reactions and the Relationship between Resin Loading Level and Catalyst Efficiency

Zhao

Shi

et al. 2004

J. Comb. Chem.

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“…Starting with 4-hydroxybenzophenone 11 , addition of phenylmagnesium bromide gave the trityl alcohol, which was alkylated with ethyl 4-bromobutanoate at the phenolic position to provide intermediate trityl ester 12 in high yield. Bromination with acetyl bromide in toluene afforded the trityl bromide, followed by treatment with Fmoc-NHOH in CH 2 Cl 2 in the presence of DIPEA to generate the Fmoc-protected hydroxylamine ester 13 .…”

Section: Resultsmentioning

confidence: 99%

A Linker for the Solid-Phase Synthesis of Hydroxamic Acids and Identification of HDAC6 Inhibitors

et al. 2017

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We herein present broadly useful, readily available and nonintegral hydroxylamine linkers for the routine solid-phase synthesis of hydroxamic acids. The developed protocols enable the efficient synthesis and release of a wide range of hydroxamic acids from various resins, relying on high control and flexibility with respect to reagents and synthetic processes. A trityl-based hydroxylamine linker was used to synthesize a library of peptide hydroxamic acids. The inhibitory effects of the compounds were examined for seven HDAC enzyme subtypes using a chemiluminescence-based assay.

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“…Since these catalysts can be expensive and laborious to synthesize, − devising flexible methods to recover and recycle them could potentially increase the utility and applicability of intramolecular hydroamination/cyclization. Although immobilizing transition metal catalysts on solid supports is well-developed, − as far as we are aware, this contribution represents the first immobilization of organolanthanide catalysts on solid phases for hydroamination/cyclization. The approach we report is unconventional and capitalizes on the distinctive, frequently rapid interconvertability characteristics of Ln−C and Ln−N bonds.…”

Section: Introductionmentioning

confidence: 99%

Recyclable Polymer-Supported Organolanthanide Hydroamination Catalysts. Immobilization and Activation via Dynamic Transamination

Zhao

Marks

2006

Organometallics

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A series of divinylbenzene cross-linked, amino-functionalized polystyrene resins such as aminomethylated polystyrenes of varying mesh size, piperazinomethyl polystyrene, 1,12-diaminododecanetrityl resin, 1,7-diaminoheptanetrityl resin, 1,2-diaminoethanetrityl resin, 1,4-bis-(aminomethyl)benzenetrityl resin, N-(2-aminoethyl)aminomethyl polystyrene, cis-1,2-diaminocyclohexanetrityl resin, and trans-1,2diaminocyclohexanetrityl resin are used as supports for the intramolecular hydroamination/cyclization precatalysts Cp′ 2 SmCH(SiMe 3 ) 2 , Cp′ 2 LaCH(SiMe 3 ) 2 (Cp′ ) η 5 -Me 5 C 5 ), and CGCSmN(SiMe 3 ) 2 (CGC ) Me 2 Si[(η 5 -Me 4 C 5 )( t BuN)]). It is shown that these catalyst precursors can be immobilized on the polymer supports via transaminative protonolysis to give the corresponding bound precatalysts, which, in the presence of aminoalkene substrates, are transaminatively released for efficient homogeneous intramolecular hydroamination/cyclization processes. Upon substrate consumption, the catalysts are readsorbed on the supports. In many cases, these catalysts exhibit activities comparable to the homogeneous precursors and are recoverable/recyclable with only minor to moderate loss of activity, depending on the particular resin amino substituents.

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An improved and general synthesis of monomers for incorporating trityl linker groups into polystyrene synthesis supports

Cited by 17 publications

References 48 publications

Polystyrene-Supported Phosphine-Catalyzed aza-Baylis−Hillman Reactions and the Relationship between Resin Loading Level and Catalyst Efficiency

Polystyrene-Supported Phosphine-Catalyzed aza-Baylis−Hillman Reactions and the Relationship between Resin Loading Level and Catalyst Efficiency

A Linker for the Solid-Phase Synthesis of Hydroxamic Acids and Identification of HDAC6 Inhibitors

Recyclable Polymer-Supported Organolanthanide Hydroamination Catalysts. Immobilization and Activation via Dynamic Transamination

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