Tetrahedron letters

Novel linker for the solid-phase synthesis of guanidines

JA Josey, CA Tarlton, CE Payne

Index: Josey, John A.; Tarlton, Catherine A.; Payne, Courtney E. Tetrahedron Letters, 1998 , vol. 39, # 33 p. 5899 - 5902

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Citation Number: 47

Abstract

A novel linker for the generation of alkyl-, acyl-and arylguanidines as an attachment point in solid phase synthesis has been developed. Introduction of a suitably functionalized thiourea to Wang resin via a carbamate linkage, followed by displacement of sulfur with a 1° or 2° amine affords resin bound guanidines suitably protected for further manipulation. Activation of the thiourea with Mukaiyama's reagent allows for the generation of arylguanidines. Mild ...