An oxidation-labile traceless linker for solid-phase synthesis

F Stieber; U Grether; H Waldmann

doi:10.1002/(SICI)1521-3773(19990419)38:8<1073::AID-ANIE1073>3.0.CO;2-Y

An oxidation-labile traceless linker for solid-phase synthesis

Angew Chem Int Ed Engl. 1999;38(8):1073-7. doi: 10.1002/(SICI)1521-3773(19990419)38:8<1073::AID-ANIE1073>3.0.CO;2-Y.

Authors

F Stieber¹, U Grether, H Waldmann

Affiliation

¹ Institut für Organische Chemie der Universität, Richard-Willstätter-Allee 2, D-76128 Karlsruhe, Germany, Fax: (+49) 721-608-4825.

Abstract

Traceless release of biaryls, acetylenes, alkenes, heterocycles, thioethers, and secondary amines from different solid supports can be achieved under very mild conditions by using a hydrazide group. This group, which is converted into an acyl diazene by oxidation and subsequently cleaved by a nucleophile (see scheme), is thus an attractive new linker for solid-phase synthesis and combinatorial chemistry.

Keywords: Antibiotics; Combinatorial chemistry; Hydrazides; Oxidations; Solid-phase synthesis.