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Literature DB >> 21250720

Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions.

Abstract

The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. α,α-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess.

Entities: Chemical

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Year: 2011 PMID： 21250720 DOI： 10.1021/jo1022469

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

13 in total

1. L-amino acid ligase from Pseudomonas syringae producing tabtoxin can be used for enzymatic synthesis of various functional peptides.

Authors: Toshinobu Arai; Yasuhiro Arimura; Shun Ishikura; Kuniki Kino
Journal: Appl Environ Microbiol Date: 2013-06-14 Impact factor: 4.792

10. New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction.

Authors: Omar Sánchez-Antonio; Kevin A Romero-Sedglach; Erika C Vázquez-Orta; Eusebio Juaristi
Journal: Molecules Date: 2020-10-03 Impact factor: 4.411

Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions.

1. L-amino acid ligase from Pseudomonas syringae producing tabtoxin can be used for enzymatic synthesis of various functional peptides.

2. Organocatalysis in water at room temperature with in-flask catalyst recycling.

Review 3. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Review 4. Mechanochemistry as an emerging tool for molecular synthesis: what can it offer?

5. Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions.

6. N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling.

7. Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach.

8. Selective enzymatic esterification of lignin model compounds in the ball mill.

Review 9. Novel Methodologies for Chemical Activation in Organic Synthesis under Solvent-Free Reaction Conditions.

10. New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction.