Formation of vicinal secondary and all-carbon quaternary stereocenters in enantioenriched diazenes via branched-selective Pd-catalyzed allylic alkylation
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1.
California Institute of Technology
Abstract
The synthesis of enantioenriched alkyl diazenes with vicinal secondary and all‑carbon quaternary stereocenters via palladium-catalyzed allylic alkylation is reported. Diazenes were formed in high diastereoselectivity and modest enantioselectivity. Notably, the ratio of branched to linear products was very high, a rarely observed phenomenon in palladium catalysis. The utility of this approach was demonstrated by cleaving the NN bond to form an α-secondary amine with a vicinal all‑carbon quaternary stereocenter.
Copyright and License
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Acknowledgement
We thank the NIH-NIC-MS (R35GM145239), the Heritage Medical Research Investigator Program, and Caltech for financial support.
Conflict of Interest
The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Brian M. Stoltz reports financial support was provided by National Institutes of Health. I, Brian M. Stoltz, am editor in chief of Tetrahedron, the sister journal to which we are submitting.
Supplemental Material
Additional Information
Dedicated to Prof. Song Lin on his receipt of the Tetrahedron Young Investigator Award 2025.
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Funding
- National Institutes of Health
- R35GM145239
- California Institute of Technology
Dates
- Accepted
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2025-05-12
- Available
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2025-05-16Available online
- Available
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2025-05-19Version of record