Proline and 1-(2-(benzoxazole-2-yl)phenyl)-3-phenylthiourea supramolecular organocatalyst in asymmetric aldol reactions

[Display omitted] •Novel chiral Self Assembled (S)-Proline and phenylthiourea organocatalyst.•Organocatalyzed enantioselective aldol reaction under solvent-free conditions.•A new approach to high-efficiency as asymmetric Aldol reaction. In this work we report the (S)-proline-thiourea 1 host–guest co...

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Bibliographic Details
Published in:Tetrahedron letters 2021-08, Vol.79, p.153301, Article 153301
Main Authors: Díaz-Juárez, Verónica, Reyes-Escobedo, Carlos Ernesto, Pérez-Venegas, Mario, Juaristi, Eusebio, Pérez-Estrada, Salvador, Rojas-Lima, Susana, López-Ruiz, Heraclio
Format: Article
Language:English
Subjects:
Asymmetric supramolecular organocatalysis
Benzoxazol moiety
Enantioselective aldol reaction
Proline
Thiourea
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Summary:[Display omitted] •Novel chiral Self Assembled (S)-Proline and phenylthiourea organocatalyst.•Organocatalyzed enantioselective aldol reaction under solvent-free conditions.•A new approach to high-efficiency as asymmetric Aldol reaction. In this work we report the (S)-proline-thiourea 1 host–guest complex as an efficient catalyst in the enantioselective aldol rection of ketones with aldehydes. This host–guest complex performs well at 0 °C, in a non-polar solvent, such as toluene, or under solvent-less conditions affording high yields (75%-86%), enantioselectivities (er > 87%) and diastereoselectivities (ds > 92%) in the asymmetric aldol reaction of ketones with aldehydes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153301