Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles
2011
Creating Functionalized Homoallylic Amines
publication
Evidence: moderate
Author Information
Author(s): Wipf Peter, Manojlovic Marija, Brummond Kay M
Primary Institution: Department of Chemistry, University of Pittsburgh
Hypothesis
Can a one-pot hydrozirconation of allenes and nitriles yield homoallylic amines?
Conclusion
The study successfully developed a method to synthesize N-unprotected homoallylic amines through a one-pot reaction.
Supporting Evidence
- The method allows for the synthesis of homoallylic amines in good yields.
- Both intermolecular and intramolecular reactions were explored.
- Products were isolated as single regio- and diastereoisomers.
Takeaway
Scientists found a way to make special amines using a simple one-step process with certain chemicals.
Methodology
The method involved hydrozirconation of allenes and nitriles followed by transmetalation with dimethylzinc or zinc chloride.
Limitations
The reaction yields varied and some substrates were unreactive.
Digital Object Identifier (DOI)
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