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Catalytic Asymmetric Aziridination of alpha,beta-Unsaturated Aldehydes
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
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2011 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 28, 7904-7917 p.Article in journal (Refereed) Published
Abstract [en]

The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99 % ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and up to 99 % ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99 % ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocyclic carbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92-99 %. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.

Place, publisher, year, edition, pages
2011. Vol. 17, no 28, 7904-7917 p.
Keyword [en]
asymmetric catalysis-aziridines; domino reactions; hydroxylamines; unsaturated aldehydes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-13899DOI: 10.1002/chem.201100042ISI: 000293383300028Scopus ID: 2-s2.0-79959645834OAI: oai:DiVA.org:miun-13899DiVA: diva2:420300
Available from: 2011-05-31 Created: 2011-05-31 Last updated: 2014-08-29Bibliographically approved

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