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Direct Regiospecific and Highly Enantioselective Intermolecular α-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts
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2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 10, 2972-2977 p.Article in journal (Refereed) Published
Abstract [en]

The first direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed.

Place, publisher, year, edition, pages
2012. Vol. 18, no 10, 2972-2977 p.
Keyword [en]
aldehydes, allylation, asymmetric catalysis, co-catalysis, transition metals
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-76269DOI: 10.1002/chem.201103366ISI: 000300837100028OAI: diva2:527421
5Available from: 2012-05-21 Created: 2012-05-10 Last updated: 2012-08-23Bibliographically approved

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Córdova, Armando
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Department of Organic Chemistry
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