What question did this study set out to answer?

Develop an asymmetric propargylic substitution strategy to construct alkynyl-substituted all-carbon quaternary stereocenters bearing adjacent tertiary stereocenters.

August 19, 2026Journal of the American Chemical Society

B/Pd-Catalyzed AsymmetricPropargylic Substitutionfor Vicinal Quaternary/Tertiary Stereocenters

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Authors

ZCZhihe Cen HLHua Liang GZGuanzhen Zhao

Discussion

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Overview

Synthetic methodology study reveals efficient boron-palladium dual-catalyzed propargylic substitution of tertiary carbonates, highlighting an approach to complex vicinal stereocenters.

Key Points

Develop an asymmetric propargylic substitution strategy to construct alkynyl-substituted all-carbon quaternary stereocenters bearing adjacent tertiary stereocenters.
Coupled tertiary propargylic carbonates with α-hydroxy ketones using a synergistic boron/palladium dual-catalytic platform.
Utilized chiral phosphoramidite-palladium complexes to establish a differentiated chiral environment and govern stereochemical selectivity.
Preserved the alkyne handle while suppressing typical allene formation to deliver vicinal quaternary/tertiary stereocenters with high diastereo- and enantiocontrol.
Overcame steric congestion to achieve precise discrimination between sterically and electronically similar alkyl groups, such as methyl versus ethyl.

Cite This Study

Cen et al. (2026) studied this question.

synapsesocial.com/papers/6a85643903308d306e2d7cea https://doi.org/10.1021/jacs.6c07657

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August 19, 2026Journal of the American Chemical Society

B/Pd-Catalyzed AsymmetricPropargylic Substitutionfor Vicinal Quaternary/Tertiary Stereocenters

View Full Paper

Ask AI

Bookmark

Authors

ZCZhihe Cen HLHua Liang GZGuanzhen Zhao

Discussion

Member takes

Overview

Synthetic methodology study reveals efficient boron-palladium dual-catalyzed propargylic substitution of tertiary carbonates, highlighting an approach to complex vicinal stereocenters.

Key Points

Develop an asymmetric propargylic substitution strategy to construct alkynyl-substituted all-carbon quaternary stereocenters bearing adjacent tertiary stereocenters.
Coupled tertiary propargylic carbonates with α-hydroxy ketones using a synergistic boron/palladium dual-catalytic platform.
Utilized chiral phosphoramidite-palladium complexes to establish a differentiated chiral environment and govern stereochemical selectivity.
Preserved the alkyne handle while suppressing typical allene formation to deliver vicinal quaternary/tertiary stereocenters with high diastereo- and enantiocontrol.
Overcame steric congestion to achieve precise discrimination between sterically and electronically similar alkyl groups, such as methyl versus ethyl.

Cite This Study

Cen et al. (2026) studied this question.

synapsesocial.com/papers/6a85643903308d306e2d7cea https://doi.org/10.1021/jacs.6c07657

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