P. Holte, L. Thijs, B. Zwanenburg
Oct 1, 1998
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron Letters
Abstract
Polymer-supported sulfonyl chloride is used in the solid-phase synthesis of disubstituted 1,3-oxazolidin-2ones. The target compounds were prepared by attaching 1,2-diols to the solid support, followed by reaction with p-toluenesulfonyl isocyanate and subsequent cyclo-elimination with concurrent detachment from the resin. Oxazolidinones of high enantiopurity can be prepared with this method by employing enantiopure 1,2diols. © 1998 Elsevier Science Ltd. All rights reserved. Solid-phase organic synthesis (SPOS) has attracted increasing attention over the past several years. 1 Combinatorial application of SPOS enables the preparation of large numbers of (structurally related) molecules in short periods of time, which is of great importance in finding new lead compounds in drug development. 2 We have focused our research efforts on the development of new methodology for the solid-phase chemistry of heterocyclic compounds. Here, we report the convenient preparation of polymer-supported sulfonyl chloride 2, which was proved to be a useful polymer-bound analogue ofp-toluenesulfonyl chloride. This polymer-supported reagent was utilized in the solid-phase synthesis of 3,5disubstituted 1,3-oxazolidin-2-ones from 1,2-diols. In recent years, there has been a considerable interest in 3,5-disubstituted 1,3-oxazolidin-2-ones as they exhibit a broad and powerful antibacterial activity) Therefore, they are interesting targets for SPOS. 4 The solid-supported reagent 2 was prepared from a commercially available sulfonic acid resin. The solution-phase preparation of sulfonyl chlorides from the corresponding sulfonates is well documented. 5a'd Recently, some solid-phase preparations of sulfonyl chlorides have been reported. 5"g These methods, however, require elevated temperatures and