What question did this study set out to answer?

To develop a divergent catalytic strategy for synthesizing [5,5] and [6,5] spiro-heterocycles by altering the fundamental reaction mode of vinylethylene carbonates.

May 10, 2018Angewandte Chemie International Edition

Palladium‐Titanium Relay Catalysis Enables Switch from Alkoxide‐π‐Allyl to Dienolate Reactivity for Spiro‐Heterocycle Synthesis

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To develop a divergent catalytic strategy for synthesizing [5,5] and [6,5] spiro-heterocycles by altering the fundamental reaction mode of vinylethylene carbonates.
Implemented a dual palladium-titanium relay catalytic system using commercially available catalysts.
Engineered an umpolung reactivity switch from conventional alkoxide-π-allyl to dienolate intermediates utilizing Lewis acid assistance.
Enabled divergent, selective pathways toward both [5,5] and [6,5] spiro-heterocyclic ring systems containing three contiguous stereocenters.
Delivered target heterocyclic products in high yields alongside uniformly excellent diastereocontrol.

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Implication

Synthetic study demonstrates dual palladium-titanium relay catalysis for spiro-heterocycle construction, highlighting an umpolung reactivity switch to access complex chiral architectures.

Cite This Study

Yang et al. (2018) studied this question.

synapsesocial.com/papers/6a98c0a64f4bbec9e275b34d https://doi.org/10.1002/anie.201804160

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Implication

Synthetic study demonstrates dual palladium-titanium relay catalysis for spiro-heterocycle construction, highlighting an umpolung reactivity switch to access complex chiral architectures.

Palladium‐Titanium Relay Catalysis Enables Switch from Alkoxide‐π‐Allyl to Dienolate Reactivity for Spiro‐Heterocycle Synthesis

Key Points

Discussion

Implication

Cite This Study

Palladium‐Titanium Relay Catalysis Enables Switch from Alkoxide‐π‐Allyl to Dienolate Reactivity for Spiro‐Heterocycle Synthesis

Key Points

Discussion

Implication

Cite This Study

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