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Expanding the scope of the elpaN-type library: glucose-derived bis(pyridine-2-carboxamide) ligands (elpaN-Py) for molybdenum-catalyzed asymmetric allylic alkylations
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2013 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 20, 4061-4065 p.Article in journal (Refereed) Published
Abstract [en]

The elpaN-Py family of ligands, which represents a subset of the elpaN-type library based on a-glucose, is described. The ligands are structural analogs of the privileged bis(pyridine-2-carboxamides) derived from trans-1,2-diaminocyclohexane, and differ for the type of substitution in the coordinating functions present in positions 1 and 2. Their ability to induce high enantioselectivity in asymmetric allylic alkylations promoted by molybdenum under microwave irradiation has been successfully demonstrated, starting from both a linear (ee up to 99%) and a branched substrate (ee up to 96%). The multifunctional nature of the sugar scaffold was exploited for the preparation of a polar ligand, through deprotection of the hydroxyl groups in positions 3, 4 and 6. In this version, it was possible to verify the performance in catalysis in alternative solvents, such as ionic liquids and water.

Place, publisher, year, edition, pages
2013. Vol. 69, no 20, 4061-4065 p.
Keyword [en]
Asymmetric catalysis, Molybdenum, Carbohydrates, Allylation, Microwave reactions
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-122500DOI: 10.1016/j.tet.2013.03.075ISI: 000317810700005ScopusID: 2-s2.0-84876158295OAI: diva2:622815

QC 20130523. Correction in: Tetrahedron, vol. 69, issue 25, pages 5259-5259.

DOI: 10.1016/j.tet.2013.04.085. WOS:000319647600027


Available from: 2013-05-23 Created: 2013-05-23 Last updated: 2014-09-15Bibliographically approved

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