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

• Dynamic systems based on interdependent nitroaldol and boronic ester reactions have beendemonstrated. In aprotic solvents, nitroalkane-1,3-diols generated by the nitroaldol reaction weresusceptible to ester formation with different boronic acids, leading to significant stabilization of theadducts under basic conditions. Hydrolysis of the boronic esters occurred in the presence of water.The boronic ester formation was stereoselective as established using diastereomericnitroalkanediols. The use of bifunctional building blocks was furthermore established, allowing formain chain nitroaldol-boronate dynamers as well as complex dynamers with distinct topologies. Theshape and rigidity of the resulting dynamers showed apparent dependency on the configuration ofthe boronic acids.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

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