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Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes
Univ Basque Country, Dept Quim Organ 1, UPV EHU, Manuel Lardizabal 3, San Sebastian 20018, Spain..
Univ Basque Country, Dept Quim Organ 1, UPV EHU, Manuel Lardizabal 3, San Sebastian 20018, Spain..
Univ Basque Country, Dept Quim Organ 1, UPV EHU, Manuel Lardizabal 3, San Sebastian 20018, Spain..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.ORCID iD: 0000-0003-2673-075X
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2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765Article in journal (Refereed) Published
Abstract [en]

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6-31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019.
Keywords [en]
asymmetric catalysis, azaarenes, Bronsted bases, hydantoins, quaternary stereocenters
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-261019DOI: 10.1002/chem.201902817ISI: 000484834700001PubMedID: 31318987Scopus ID: 2-s2.0-85072225163OAI: oai:DiVA.org:kth-261019DiVA, id: diva2:1359695
Note

QC 20191010

Available from: 2019-10-10 Created: 2019-10-10 Last updated: 2019-10-10Bibliographically approved

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Brinck, ToreDinér, Peter

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