Diastereoselective Synthesis of Highly Functionalized Proline Derivatives

Philippova, Anna N.; Vorobyeva, Daria V.; Gribanov, Pavel S.; Dolgushin, Fedor M.; Osipov, Sergey N.

doi:10.3390/molecules27206898

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2023

2024

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Cited by 3 publications

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Rh(III)‐Catalyzed Annulation of (Het)aryl Amides with α‐Allenyl‐Containing α‐Amino Acid Derivatives

Vorobyeva,

Bubnova,

Godovikov

et al. 2024

Asian J Org Chem

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An efficient pathway to a new series of CF3‐substituted α‐amino acid derivatives decorated with pharmacophore isoquinolone and pyrimido[1,6‐a]indolone cores has been developed. The method includes Rh(III)‐catalyzed C‐H activation/[4+2]‐annulation of N‐(pivaloyloxy)‐substituted aryl hydroxamates and indole‐1‐carboxamides with readily available allenyl‐containing α‐amino carboxylates and their phosphorus analogues. It was established that the reactions occur via Rh‐σ‐alkenyl intermediates to provide new C‐C bond forming process with the participation of terminal carbon atom of allene moiety.

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