Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

Valverde, Ibai E.; Delmas, A.F.; Aucagne, Vincent

doi:10.1016/j.tet.2009.06.093

Cited by 66 publications

(66 citation statements)

References 46 publications

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“…35 First, propargyl bromide was deprotonated with n-butyllithium before reacting it with the corresponding chlorotrialkylsilane (a: trimethylsilyl chloride (61%); b: triisopropylsilyl chloride (59%)). Norborneneimide 3 was prepared and N-alkylated using 4 and SI1a,b to give monomers 5 (83%) and SI2a,b (84% and 75%) according to a literature procedure.…”

Section: Resultsmentioning

confidence: 99%

ROMP Copolymers for Orthogonal Click Functionalizations

2012

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ABSTRACT:The ring-opening metathesis polymerization using ruthenium carbene initiators developed by Grubbs et al. is one of the most functional group tolerant living polymerization methods known. One of the most used postpolymerization functionalization methods used today is the copper-catalyzed 1,3-dipolar cycloaddition between alkynes and organic azides. Organic azides are, however, not tolerated by ruthenium carbene initiators, and nonprotected alkynes have been shown to slow down the propagation reaction or react with the propagating species leading to broad molecular weight distributions. Here we report the copolymer synthesis of three orthogonally functionalizable monomers: one carrying an activated pentafluorophenyl ester, one a maleimide unit, and a third one a trialkylsilyl-protected alkyne. From these monomers, statistical terpolymers as well as diblock copolymers were synthesized with different molecular weights and monomer compositions or block ratios, respectively. Excellent control over molecular weight and molecular weight distribution could be achieved using Grubbs' firstgeneration ruthenium carbene initiator. Herein we present the synthesis and orthogonal triple postpolymerization functionalization of these copolymers.

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Section: Resultsmentioning

confidence: 99%

ROMP Copolymers for Orthogonal Click Functionalizations

2012

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“…We and others have shown that triisopropylsilyl (TIPS) is a group of choice for multiple linear CuAAC steps, [16] and we have demonstrated its full compatibility with the conditions of fluorenylmethoxycarbonyl (Fmoc) SPPS.…”

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confidence: 86%

Synthesis of a Biologically Active Triazole‐Containing Analogue of Cystatin A Through Successive Peptidomimetic Alkyne–Azide Ligations

Valverde¹,

Lecaille²,

Lalmanach³

et al. 2011

Angew Chem Int Ed

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“…Complete removal of the TBDMS groups could be mediated by the cop-per salt in polar protic solvent. [51] We then attempted the cycloaddition using condition B; fortunately, the desired compound 12 was obtained in 67 % yield without affecting the TBDMS group.…”

Section: Resultsmentioning

confidence: 99%

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

Ward

Ling

2011

Eur J Org Chem

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The perfunctionalization of the secondary face of cyclodextrins (CDs) is a challenging task that often results in poor yields. Here, we report that the use of copper‐catalyzedHuisgen 1,3‐dipolar cycloaddition is an efficient and versatile strategy that provides perfunctionalized CDs at the secondary face with good to high yields. A variety of functional groups, such as alkyl, alkenyl, ester, carboxylic acid, amide, and alcohol, have been successfully incorporated on the secondary face of β‐CD from the same starting material. These functionalized CD derivatives could be used as building blocks for further structural modification or as hosts for different applications.

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Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

Cited by 66 publications

References 46 publications

ROMP Copolymers for Orthogonal Click Functionalizations

ROMP Copolymers for Orthogonal Click Functionalizations

Synthesis of a Biologically Active Triazole‐Containing Analogue of Cystatin A Through Successive Peptidomimetic Alkyne–Azide Ligations

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

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