Templates Derived from the Baylis-Hillman Reaction

By immobilizing 3-(n-butyl) 4-isopropoxy squarate instead of diisopropyl squarate, naphthalines were accessible. Thermolysis and air oxidation of this resin-bound substrate gave a 1,4-naphthoquinone derivative (Fig. 6.3). If the hydroxy function was acylat-ed first, no air oxidation was possible during thermolysis and 1,4-dihydroxynaphthalines were obtained (Fig. 6.3). Both compounds were cleaved from resin with 20% TFA in CH2C12. 

3 Templates Derived from the Baylis-Hillman Reaction 

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The polymer-bound 2-arylsulfonylaminomethyl acrylic acids derived from the three-component Baylis-Hillman reaction can also be used as templates for the synthesis of different core structures. Here, we present the alkylation of these templates as an example (Fig. 6.13). 

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