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J Am Chem Soc. 2011 Jun 29;133(25):9646-9. doi: 10.1021/ja201844c. Epub 2011 Jun 6.

Design and synthesis of highly reactive dienophiles for the tetrazine-trans-cyclooctene ligation.

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  • 1Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.

Abstract

Computation was used to design a trans-cyclooctene derivative that displays enhanced reactivity in the tetrazine-trans-cycloctene ligation. The optimized derivative is an (E)-bicyclo[6.1.0]non-4-ene with a cis-ring fusion, in which the eight-membered ring is forced to adopt a highly strained 'half-chair' conformation. Toward 3,6-dipyridyl-s-tetrazine in MeOH at 25 °C, the strained derivative is 19 and 27 times more reactive than the parent trans-cyclooctene and 4E-cyclooct-4-enol, respectively. Toward 3,6-diphenyl-s-tetrazine in MeOH at 25 °C, the strained derivative is 160 times more reactive than the parent trans-cyclooctene.

PMID:
21599005
PMCID:
PMC3230318
DOI:
10.1021/ja201844c
[PubMed - indexed for MEDLINE]
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