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Synfacts 2006(1): 0085-0085
DOI: 10.1055/s-2005-921704
DOI: 10.1055/s-2005-921704
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Solid-Phase Functionalization of Soluble Polymers
J. K. Pontrello, M. J. Allen, E. S. Underbakke, L. L. Kiessling*
University of Wisconsin, Madison, USA
Further Information
Publication History
Publication Date:
16 December 2005 (online)
Significance
The authors have reported the solid-phase functionalization of soluble polymers with an N-hydroxysuccinimidyl ester-substituted block (for functionalization) and a maleimide-substituted block (for anchoring to the resin). The microwave-assisted Diels-Alder reaction of copolymers 2a or 2b with Rink amide polystyrene resin 1 gave resin-supported compound 3 in >90% yields. Amidation of resins 3a and 3b with amine followed by the irreversible Diels-Alder reaction with cyclopentadiene for liberation from the support resulted in complete polymer release to afford 5a and 5b in 96% and 97% yields, respectively.