Tripeptides as Efficient Asymmetric Catalysts for 1,4-Addition Reactions of Aldehydes to Nitroolefins-A Rational Approach

Bridging the gap: Conformational analysis of a peptidic catalyst for aldol reactions led to the development of H‐D‐Pro‐Pro‐Asp‐NH2 as a highly efficient catalyst for conjugate addition reactions between aldehydes and nitroolefins (see scheme). Only 1 mol % of catalyst suffices to obtain γ‐nitroaldeh...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-02, Vol.47 (10), p.1871-1874
Main Authors: Wiesner, Markus, Revell, Jefferson D, Wennemers, Helma
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkenes - chemical synthesis
Alkenes - chemistry
asymmetric synthesis
Catalysis
conjugate additions
Models, Chemical
Molecular Structure
Nitro Compounds - chemical synthesis
Nitro Compounds - chemistry
Oligopeptides - chemistry
organocatalysis
peptides
Stereoisomerism
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Summary:Bridging the gap: Conformational analysis of a peptidic catalyst for aldol reactions led to the development of H‐D‐Pro‐Pro‐Asp‐NH2 as a highly efficient catalyst for conjugate addition reactions between aldehydes and nitroolefins (see scheme). Only 1 mol % of catalyst suffices to obtain γ‐nitroaldehydes in excellent yields and stereoselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200704972