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Anion-π Catalysts with Axial Chirality.

Chao Wang¹, Stefan Matile¹

¹Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|August 11, 2017

Summary

Axial chirality in anion-π catalysts enhances asymmetric catalysis. This study introduces novel catalysts with axial chirality, achieving unprecedented enantioselectivity in enolate additions.

Keywords:

anion-π interactions atropisomers axial chirality catalysis enolate chemistry

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Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Anion-π catalysis stabilizes anionic transition states using aromatic surfaces.
Asymmetric anion-π catalysis typically employs stereogenic centers on π-acidic surfaces.
Previous methods struggled to achieve high enantioselectivity with small-molecule catalysts.

Purpose of the Study:

To introduce the first anion-π catalysts utilizing axial chirality.
To evaluate the efficacy of axial chirality compared to point chirality in asymmetric anion-π catalysis.
To explore the relationship between π-surface acidity and enantioselectivity.

Main Methods:

Design and synthesis of bifunctional anion-π catalysts with tertiary amine bases and naphthalenediimide planes.
Incorporation of bulky aromatic substituents to create separable atropisomers (axial chirality).
Evaluation of catalyst performance using the addition of malonic acid half thioesters to enolate acceptors.

Main Results:

Catalysts with axial chirality demonstrated significantly improved selective acceleration of enolate addition compared to point chirality.
Enantioselectivity was achieved for the first time in this reaction using small-molecule anion-π catalysts.
Higher π-acidity of the aromatic surface correlated with increased enantioselectivity.

Conclusions:

Axial chirality, specifically through atropisomerism, is a highly effective strategy for asymmetric anion-π catalysis.
The developed catalysts offer a promising new avenue for enantioselective synthesis.
Catalyst design focusing on the π-surface properties is crucial for optimizing enantioselectivity.