Palladium-Catalyzed Enantioselective Synthesis of Chiral Vinylallenes via γ-Selective Coupling of Vinylboronates with Propargylic Carbonates.

Authors

Changwen Yan, Zixuan Liu, Chenyang Lu, Zheng Liu, Hui Zhang, Xiaoyu Wu

Published in

Organic letters. Volume 28. Issue 43. Pages 13592-13597. Oct 30, 2026.

Abstract

We report a palladium/phosphoramidite-catalyzed asymmetric γ-selective cross-coupling of racemic propargylic carbonates with alkenyl boronates for the synthesis of axially chiral vinylallenes. This transformation provides a direct and modular entry to densely substituted vinylallenes under mild conditions, furnishing the desired products in good to excellent yields and high enantioselectivities (up to 91% yield and 95% ee). A broad range of propargylic carbonates and cyclic, styrenyl, and functionalized alkenyl boronates are well tolerated. The synthetic utility of the method is demonstrated by a mmol-scale reaction and downstream transformations of the vinylallene products.

PMID:
42960927
Bibliographic data and abstract were imported from PubMed on 30 Oct 2026.

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