Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies.

Autor: Karalius A; Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 36, S-10044, Stockholm, Sweden., Qi Y; Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, MA, 01854, USA., Ayinla M; Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, MA, 01854, USA., Szabó Z; Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 36, S-10044, Stockholm, Sweden., Ramström O; Department of Chemistry, KTH - Royal Institute of Technology, Teknikringen 36, S-10044, Stockholm, Sweden.; Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, MA, 01854, USA.; Department of Chemistry and Biomedical Sciences, Linnaeus University, SE-39182, Kalmar, Sweden.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Nov 12; Vol. 30 (63), pp. e202402409. Date of Electronic Publication: 2024 Oct 23.
DOI: 10.1002/chem.202402409
Abstrakt: Complex dynamic systems displaying interdependency between nitroaldol and boronic ester reactions have been demonstrated. Nitroalkane-1,3-diols, generated by the nitroaldol reaction, were susceptible to ester formation with different boronic acids in aprotic solvents, whereas hydrolysis of the esters occurred in the presence of water. The boronic ester formation led to significant stabilization of the nitroaldol adducts under basic conditions. The use of bifunctional building blocks was furthermore established, allowing for main chain nitroaldol-boronate dynamers as well as complex network dynamers with distinct topologies. The shape and rigidity of the resulting dynamers showed an apparent dependency on the configuration of the boronic acids.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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