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

Citation
G. Faita et al., (4S)-p-hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions, TETRAHEDR L, 41(8), 2000, pp. 1265-1269
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
8
Year of publication
2000
Pages
1265 - 1269
Database
ISI
SICI code
0040-4039(20000219)41:8<1265:(AASCA>2.0.ZU;2-W
Abstract
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.