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Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization.

ABSTRACT: The development and application of a novel endo furan-protected maleimide building block is reported. The endo isomer undergoes deprotection at temperatures ?50 °C below the exo derivative. This enables a simple and powerful approach to quantitatively and selectively introduce functional maleimide groups via temperature modulation.

SUBMITTER: Discekici EH 

PROVIDER: S-EPMC6205238 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization.

Discekici Emre H EH   St Amant Andre H AH   Nguyen Shay N SN   Lee In-Hwan IH   Hawker Craig J CJ   Read de Alaniz Javier J  

Journal of the American Chemical Society 20180403 15

The development and application of a novel endo furan-protected maleimide building block is reported. The endo isomer undergoes deprotection at temperatures ∼50 °C below the exo derivative. This enables a simple and powerful approach to quantitatively and selectively introduce functional maleimide groups via temperature modulation. ...[more]

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