Tetrahydropyran-Based Hybrid Dipeptides as Asymmetric Catalysts for Michael Addition of Aldehydes to [beta]-Nitrostyrenes

A new series of hybrid dipeptide-like organocatalysts based on pyranoid - or [zeta]-amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to [beta]-nitrostyrenes. The reaction proceeds under mild conditions to afford a wide range of [gamma]-nitroaldehydes with u...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-02, Vol.359 (4), p.576-583
Main Authors: Borges-Gonzalez, Jorge, Feher-Voelger, Andrés, Crisostomo, Fernando Pinacho, Morales, Ezequiel Q, Martin, Tomás
Format: Article
Language:English
Subjects:
Aldehydes
Amino acids
Asymmetry
Carboxylic acids
Catalysis
Catalysts
Proline
Selectivity
Synthesis (chemistry)
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Summary:A new series of hybrid dipeptide-like organocatalysts based on pyranoid - or [zeta]-amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to [beta]-nitrostyrenes. The reaction proceeds under mild conditions to afford a wide range of [gamma]-nitroaldehydes with up to 98% yield and up to 96% ee. These dipeptides are bifunctional organocatalysts, with a proline at the N-terminus and a carboxylic acid at the C-terminus. The tetrahydropyran unit embedded in the - or [zeta]-amino acid induces a well-defined conformation that is responsible for the catalysis. These dipeptides represent a new type of organocatalyst with a large number of possibilities to modulate their reactivity and selectivity.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201601193