5-(Trimethylsilyl)-1,3-cyclopentadiene

Palácios, Francisco; Santos, Jesús M. de los

doi:10.1002/047084289x.rn01739

Encyclopedia of Reagents for Organic Synthesis 2014

DOI: 10.1002/047084289x.rn01739

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5-(Trimethylsilyl)-1,3-cyclopentadiene

Francisco Palácios

Jesús M. de los Santos

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2022

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Cited by 1 publication

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“…We believe that these peaks correspond to DA isomers in which the TMS group is not at its original position and thus would not have the same rate enhancement for the retro-DA reaction that the parent isomer does . We speculate that the unproductive forward-DA reaction with more electron deficient acrylamides is competitive with the evaporation of TMS-CP under these reaction conditions . Based upon our kinetic studies, we thought the retro-DA would achieve near full conversion sooner than 90 min and prolonged reaction times would not be beneficial.…”

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Thermal Stability and Utility of Dienes as Protecting Groups for Acrylamides

Hooper

Burns

2022

ACS Med. Chem. Lett.

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Acrylamides are privileged electrophiles used in targeted covalent therapies, often installed at the end of a synthetic sequence due to their reactive nature. Herein, we report several diene-acrylamide adducts with a range of thermal stabilities toward retro-Diels−Alder deprotection of the acrylamide, enabling this masked functionality to be introduced early in a synthetic route and deprotected in a specific temperature range. Through kinetic studies, we identify solvent and structural trends that impact the stability of trimethylsilyl cyclopentadiene (TMS-CP) acrylamide adducts. TMS-CP protected acrylamides were installed on several amine-containing drugs, whose acrylamides were thermally unveiled (T = 160 °C, time ≤ 1 h) in moderate to high yields. We also showcase the potential utility of this protection strategy by improving the yield of a base-promoted S N Ar reaction when the acrylamide is masked.

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Thermal Stability and Utility of Dienes as Protecting Groups for Acrylamides

Hooper

Burns

2022

ACS Med. Chem. Lett.

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5-(Trimethylsilyl)-1,3-cyclopentadiene

Cited by 1 publication

References 87 publications

Thermal Stability and Utility of Dienes as Protecting Groups for Acrylamides

Thermal Stability and Utility of Dienes as Protecting Groups for Acrylamides

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