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Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalizationoa mark
  • Discekici, Emre H. ;
  • St. Amant, Andre H. ;
  • Nguyen, Shay N. ;
  • Lee, In Hwan ;
  • Hawker, Craig J. ;
  • Read De Alaniz, Javier
Citations

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Publication Year
2018-04-18
Publisher
American Chemical Society
Citation
Journal of the American Chemical Society, Vol.140, pp.5009-5013
Mesh Keyword
Building blockesChemical functionalizationDeprotectionDevelopment and applicationsDiels Alder AdductsEndo isomersMaleimide groupTemperature modulation
All Science Classification Codes (ASJC)
CatalysisChemistry (all)BiochemistryColloid and Surface Chemistry
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.
Language
eng
URI
https://dspace.ajou.ac.kr/dev/handle/2018.oak/30185
DOI
https://doi.org/10.1021/jacs.8b01544
Fulltext

Type
Article
Funding
J.R.A. and C.J.H. acknowledge support from the UCSB MRSEC (NSF DMR 1720256). E.H.D. thanks the NSF Graduate Research Fellowship and the UCSB graduate division, Graduate Research Mentorship Program (GRMP) fellowship for financial support. A.H.S. thanks the Natural Sciences and Engineering Research Council of Canada (NSERC) for a postgraduate scholarship (PGS-D). S.N.N. thanks the MARC scholars program.
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Lee, In-Hwan 이인환
Department of Chemistry
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