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Carbohydrate-Based Pyridine-2-carboxamides for Mo-Catalyzed Asymmetric Allylic Alkylations
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
2009 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 9, 1352-1356 p.Article in journal (Refereed) Published
Abstract [en]

Bis(pyridine-2-carboxamides) were prepared from 1,2-diamines obtained from alpha-D-ghlcose and alpha-D-mannose. The ligands were assessed in molybdenum-catalyzed asymmetric allylic alkylations (AAA) by using both methyl (E)-3-phenyl-2-propenyl and methyl rac-1-phenyl-2-propenyl carbonates and dimethyl malonate as nucleophile under microwave irradiation. High enantioselectivity (99 % ee) and high regioselectivity (49:1 in favour of the branched isomer) were observed in reactions of the linear achiral substrate in the presence of 10 mol-% of a catalyst prepared from a ligand derived from glucose. Somewhat lower enantioselectivity (up to 96 % ee) was observed in reactions with the branched racemic carbonate by using the same ligand. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Place, publisher, year, edition, pages
2009. no 9, 1352-1356 p.
URN: urn:nbn:se:kth:diva-18309DOI: 10.1002/ejoc.200801240ISI: 000264683800010ScopusID: 2-s2.0-63449116735OAI: diva2:336355
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2010-12-17Bibliographically approved

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