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

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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Veröffentlicht in:Organic letters 2005-03, Vol.7 (6), p.1101-1103
Hauptverfasser: Krattiger, Philipp, Kovasy, Roman, Revell, Jefferson D, Ivan, Stanislav, Wennemers, Helma
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Amines - chemistry
Catalysis
Molecular Structure
Peptides - chemistry
Proline - chemistry
Stereoisomerism
Structure-Activity Relationship
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container_end_page 1103
container_issue 6
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container_title Organic letters
container_volume 7
creator Krattiger, Philipp
Kovasy, Roman
Revell, Jefferson D
Ivan, Stanislav
Wennemers, Helma
description 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.
doi_str_mv 10.1021/ol0500259
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subjects Aldehydes - chemistry
Amines - chemistry
Catalysis
Molecular Structure
Peptides - chemistry
Proline - chemistry
Stereoisomerism
Structure-Activity Relationship
title Increased Structural Complexity Leads to Higher Activity:  Peptides as Efficient and Versatile Catalysts for Asymmetric Aldol Reactions
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