Catalytic asymmetric aziridination of α,β-unsaturated aldehydes
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
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 upto 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-heterocycliccarbene 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.
asymmetric catalysisaziridines, domino reactions, hydroxylamines, unsaturated aldehydes
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-61949DOI: 10.1002/chem.201100042ISI: 000293383300028OAI: oai:DiVA.org:su-61949DiVA: diva2:438984
FunderSwedish Research Council