What question did this study set out to answer?

The aim is to achieve stereodivergence from the same substrates using a single-catalyst system.

March 29, 2026Journal of the American Chemical Society

Stereodivergent Inverse Electron-Demand Diels–Alder Reactions Enabled by Modification of Prolinol-Derived Catalysts

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Authors

EMEnrico MarcantonioAarhus University RBRené Slot BitschAarhus University AKAnne KristensenAarhus University

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Implication

This research demonstrates achieving stereodivergence in asymmetric synthesis using modified prolinol catalysts, indicating effective control over diastereoisomer formation.

Key Points

The aim is to achieve stereodivergence from the same substrates using a single-catalyst system.
Modified prolinol-derived catalysts were used in enamine-mediated reactions.
Inverse electron-demand Diels–Alder reactions were performed with aldehydes and electron-deficient dienes.
Catalyst modification involved changing the bulkiness of the β′-substituent.
Both computational and experimental studies were conducted to analyze the mechanisms.
All four stereoisomers of the cycloadduct were successfully obtained using enantiomers of the catalysts.
The reactions allowed for the formation of all eight stereoisomers with high to excellent yields.
Enantioselectivity reached over 99% ee.
Mechanistic studies revealed a catalyst-dependent dichotomy influencing stereodivergence.

Cite This Study

Marcantonio et al. (2026) studied this question.

synapsesocial.com/papers/69c8c399de0f0f753b39e71a https://doi.org/10.1021/jacs.6c01539

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Implication

This research demonstrates achieving stereodivergence in asymmetric synthesis using modified prolinol catalysts, indicating effective control over diastereoisomer formation.

Stereodivergent Inverse Electron-Demand Diels–Alder Reactions Enabled by Modification of Prolinol-Derived Catalysts

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Member takes

Implication

Key Points

Cite This Study

Stereodivergent Inverse Electron-Demand Diels–Alder Reactions Enabled by Modification of Prolinol-Derived Catalysts

Discussion

Member takes

Implication

Key Points

Cite This Study

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