(4S)-p-hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions

Evans' chiral auxiliary was grafted onto both Merrifield and Wang resins an d, after functionalisation, they were used as chiral dipolarophiles in a 1, 3-dipolar cycloaddition involving both a nitrile oxide and a nitrone. The c ycloadducts were cleaved and analysed by chiral HPLC: the recovered support ed chiral oxazolidinone was functionalised and reused in further cycloaddit ions. The stereochemical results as well as the possibility of recycling th e chiral linker supports the applicability of solid-supported chiral auxili aries. (C) 2000 Elsevier Science Ltd. All rights reserved.