Evans' chiral auxiliary was grafted onto both Merrifield and Wang resins and, after functionalisation, they were used as chiral dipolarophiles in a 1,3-dipolar cycloaddition involving both a nitrile oxide and a nitrone. The cycloadducts were cleaved and analysed by chiral HPLC: the recovered supported chiral oxazolidinone was functionalised and reused in further cycloadditions. The stereochemical results as well as the possibility of recycling the chiral linker supports the applicability of solid-supported chiral auxiliaries. (C) 2000 Elsevier Science Ltd.
(4S)-p-Hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions / G. Faita, A. Paio, P. Quadrelli, F. Rancati, P. Seneci. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 41:8(2000), pp. 1265-1269.
|Titolo:||(4S)-p-Hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions|
SENECI, PIERFAUSTO (Ultimo)
|Parole Chiave:||Asymmetric induction; Cycloadditions; Oxazolidinones; Solid-phase synthesis|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2000|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0040-4039(99)02265-0|
|Appare nelle tipologie:||01 - Articolo su periodico|