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Synfacts 2025; 21(10): 1031
DOI: 10.1055/a-2680-9371
Polymer-Supported Synthesis

An Enantioselective Cross-Aldol Reaction Using an Aminomethyl-Polystyrene-Supported Tripeptide

Authors

Yuan M, Ding T-Y, Liu Y-X, Du Z-H, Liana T-R, Da C-S *. Lanzhou University, P. R. China
Resin-Supported Peptide-Catalyzed Asymmetric Aldol Reaction of Aldehydes for the Synthesis of (R)-Pantolactone.

Org. Biomol. Chem. 2025;
23: 6191-6199
DOI: 10.1039/d5ob00706b
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Keywords

resin-supported peptides - organocatalyst - enantioselective cross-aldol reaction

Significance

An aminomethyl-polystyrene-supported tripeptide (PS-AM-TP) promoted the enantioselective cross-aldol reaction of aldehydes with glyoxylates or 2-ketoaldehydes in MeCN or H2O to afford the corresponding aldol products in up to 99 % yield and up to 99 % ee (eq. 1). When the reaction of isobutylaldehyde with ethyl glyoxylate was performed using PS-AM-ent-TP, ent-1 was obtained in 94 % yield and 98 % ee.


 

Comment

In the synthesis of 1, the catalyst was recovered and reused nine times with high enantioselectivity, although the catalytic reactivity gradually decreased. The authors previously reported the preparation of homogeneous tripeptide catalysts and their application in enantioselective cross-aldol reactions (Org. Lett. 2020, 22, 4444).


 

 

Publikationsverlauf

Artikel online veröffentlicht:
23. September 2025

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