Increased Structural Complexity Leads to Higher Activity:  Peptides as Efficient and Versatile Catalysts for Asymmetric Aldol Reactions

Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions:  (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catal...

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Bibliographic Details
Published in:Organic letters 2005-03, Vol.7 (6), p.1101-1103
Main Authors: Krattiger, Philipp, Kovasy, Roman, Revell, Jefferson D, Ivan, Stanislav, Wennemers, Helma
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amines - chemistry
Catalysis
Molecular Structure
Peptides - chemistry
Proline - chemistry
Stereoisomerism
Structure-Activity Relationship
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Summary:Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions:  (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catalysts can be changed from (R)- to (S)-selectivity by simple modifications of the secondary structure.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0500259