What question did this study set out to answer?

To determine whether weakly coordinating amine additives can improve diastereoselectivity during palladium-catalyzed carboiodination of chiral N-allyl carboxamides.

June 10, 2014Angewandte Chemie International Edition

Additive Effects in the Palladium‐Catalyzed Carboiodination of Chiral N‐Allyl Carboxamides

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To determine whether weakly coordinating amine additives can improve diastereoselectivity during palladium-catalyzed carboiodination of chiral N-allyl carboxamides.
Evaluated tertiary amines as weakly coordinating additive ligands in the Pd/QPhos-catalyzed carboiodination of chiral N-allyl carboxamides.
Applied the optimized catalytic methodology toward the asymmetric formal synthesis of the alkaloid (+)-corynoline.
Tertiary amines acted as weakly coordinating ligands that significantly enhanced diastereoselectivity during carbon-halogen reductive elimination from Pd(II).
The method enabled efficient, enantioenriched preparation of densely functionalized dihydroisoquinolinones and supported an asymmetric formal synthesis of (+)-corynoline.

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Implication

Experimental study reveals tertiary amine additives enhance diastereoselectivity in palladium-catalyzed carboiodination, facilitating the asymmetric synthesis of complex dihydroisoquinolinones.

Cite This Study

Petrone et al. (2014) studied this question.

synapsesocial.com/papers/6a8ae215f71b672e3df452d0 https://doi.org/10.1002/anie.201404007

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Implication

Experimental study reveals tertiary amine additives enhance diastereoselectivity in palladium-catalyzed carboiodination, facilitating the asymmetric synthesis of complex dihydroisoquinolinones.

Additive Effects in the Palladium‐Catalyzed Carboiodination of Chiral N‐Allyl Carboxamides

Key Points

Discussion

Implication

Cite This Study

Additive Effects in the Palladium‐Catalyzed Carboiodination of Chiral N‐Allyl Carboxamides

Key Points

Discussion

Implication

Cite This Study

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