Asymmetric aldol reactions catalyzed by efficient and recyclable silica-supported proline-based peptides

A series of silica‐supported proline‐based peptides were synthesized and applied as catalysts for direct asymmetric intermolecular aldol reactions. Among these, a peptide with two L‐proline units was found to be the most efficient one for the asymmetric aldol reactions between acetone and aromatic a...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2009-04, Vol.21 (4), p.413-420
Main Authors: Yan, Jincan, Wang, Lei
Format: Article
Language:English
Subjects:
Acetone - chemistry
Aldehydes - chemistry
asymmetric aldol reactions
Catalysis
Chemistry, Organic - methods
Magnetic Resonance Spectroscopy
Models, Chemical
Peptides - chemistry
Proline - chemistry
proline-based peptides
silica-supported catalyst
Silicon Dioxide - chemistry
Solvents
Stereoisomerism
Ultraviolet Rays
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Summary:A series of silica‐supported proline‐based peptides were synthesized and applied as catalysts for direct asymmetric intermolecular aldol reactions. Among these, a peptide with two L‐proline units was found to be the most efficient one for the asymmetric aldol reactions between acetone and aromatic aldehydes. The reactions generated the corresponding products with satisfactory isolated yields (up to 97%) and enantiomeric excesses (up to 96%) in the presence of this catalyst (5 mol %). Furthermore, the silica‐supported organocatalyst could be recovered and recycled by a simple filtration of the reaction solution and used for five consecutive trials without loss of its reactivity. Chirality, 2009. © 2008 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20603