Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference

The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3‐bis(2,4,6‐triisopropylphenyl)‐1,1‐binaphthyl‐2,2‐diyl hydrogenphosphate (TRIP) has been extended to non‐cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% an...

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Detalles Bibliográficos
Autores principales: Lazzarotto, Mattia, Hartmann, Peter, Pletz, Jakob, Belaj, Ferdinand, Kroutil, Wolfgang, Payer, Stefan E., Fuchs, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Updates
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359974/
https://www.ncbi.nlm.nih.gov/pubmed/34413715
http://dx.doi.org/10.1002/adsc.202100037
Descripción
Sumario:The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3‐bis(2,4,6‐triisopropylphenyl)‐1,1‐binaphthyl‐2,2‐diyl hydrogenphosphate (TRIP) has been extended to non‐cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% and two stereogenic centers can be created. Compared to the previous lactone reagent the stereopreference switches almost completely, proving the fact that the nature of the organometallic compound is of immense importance for the asymmetry of the product. [Image: see text]

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