Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters. Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes.

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ID: 4703
2019
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Abstract
Bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford aldol adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (dr 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 H-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.
Reference Key
izquierdo2019asymmetricchemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Izquierdo, June;Demurget, Noémie;Landa, Aitor;Brinck, Tore;Mercero, Jose M;Dinér, Peter;Oiarbide, Mikel;Palomo, Claudio;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2019
DOI
10.1002/chem.201902817
URL
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