Asymmetric Diels–Alder reaction of α,β-unsaturated oxazolidin-2-one derivatives catalyzed by a chiral Fe(III)-bipyridine diol complex

Authors: Li, MaoCarreras, VirginieJalba, AngelaOllevier, Thierry
Abstract: An asymmetric FeIII-bipyridine diol catalyzed Diels–Alder reaction of α,β-unsaturated oxazolidin-2-ones has been developed. Among various FeII/FeIII salts, Fe(ClO4)3·6H2O was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO4)3·6H2O and 2.4 mol % of Bolm’s ligand) afforded high yields (up to 99%) and high enantiomeric excesses (up to 98%) of endo-cycloadducts for the Diels–Alder reaction between cyclopentadiene and substituted acryloyloxazolidin-2-ones. Other noncyclic dienes led to decreased enantioselectivities. A proposed model supports the observed stereoinduction.
Document Type: Article de recherche
Issue Date: 8 February 2018
Open Access Date: 8 February 2019
Document version: AM
This document was published in: Organic letters, Vol. 20 (4), 995-998 (2018)
ACS Publications
Alternative version: 10.1021/acs.orglett.7b03939
Collection:Articles publiés dans des revues avec comité de lecture

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