Diastereo‐ and Enantioselective 1,4‐Difunctionalization of Borylenynes by Catalytic Conjunctive Cross‐Coupling

Enantioselective conjunctive cross‐coupling of enyne‐derived boronate complexes occurs with 1,4 addition of the electrophile and migrating group across the π system. This reaction pathway furnishes α‐boryl allenes as the reaction product. In the presence of a chiral catalyst, both the central and ax...

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Bibliographic Details
Published in:Angewandte Chemie 2020-06, Vol.132 (26), p.10397-10401
Main Authors: Law, Chunyin, Kativhu, Elton, Wang, Johnny, Morken, James P.
Format: Article
Language:English
Subjects:
boronates
Catalysts
Chemistry
Chirality
Cross coupling
Enantiomers
homogeneous catalysis
palladium
Reaction products
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Summary:Enantioselective conjunctive cross‐coupling of enyne‐derived boronate complexes occurs with 1,4 addition of the electrophile and migrating group across the π system. This reaction pathway furnishes α‐boryl allenes as the reaction product. In the presence of a chiral catalyst, both the central and axial chirality of the product can be controlled during product formation. Chiral Allenes: 1,4‐Addition of the migrating group and electrophile across an enyne‐derived boronate complex occurs during the course of Pd‐catalyzed conjunctive cross‐coupling. This process generates chiral allenyl boronic esters with control of both axial and central chirality.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202001580