Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels–Alder reaction

A novel family of chiral imidazolium-based ionic liquids containing a chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels–Alder reaction to give good yields and mode...

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Bibliographic Details
Published in:Tetrahedron 2009-03, Vol.65 (11), p.2260-2265
Main Authors: Nguyen Van Buu, Olivier, Aupoix, Audrey, Vo-Thanh, Giang
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:A novel family of chiral imidazolium-based ionic liquids containing a chiral moiety and a free hydroxyl function has been designed and synthesized using isosorbide as a biorenewable substrate. These chiral ionic liquids were found to catalyze the aza Diels–Alder reaction to give good yields and moderate diastereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.01.055