Good Selectivity in Ugi Reactions of Cyclic Imines
Author Information
Author(s): Banfi Luca, Basso Andrea, Cerulli Valentina, Rocca Valeria, Riva Renata
Primary Institution: Department of Chemistry and Industrial Chemistry, University of Genova
Hypothesis
Can 2-substituted dihydrobenzoxazepines exhibit good diastereoselectivity in Ugi reactions despite the distance between stereogenic centers?
Conclusion
The study found that Ugi reactions of 2-substituted dihydrobenzoxazepines can achieve high diastereoselectivity, with ratios up to 9:1.
Supporting Evidence
- The Ugi reaction of 2-substituted dihydrobenzoxazepines showed diastereoisomeric ratios up to 9:1.
- This is the first example of 1,4 asymmetric induction in an Ugi reaction.
- The methodology allows for the diversity-oriented synthesis of various tetrahydrobenzoxazepines.
Takeaway
This research shows that certain chemical reactions can create different versions of a molecule, even when the parts are far apart, which is pretty cool!
Methodology
The study involved synthesizing chiral 7-membered cyclic imines and testing their diastereoselectivity in Ugi reactions.
Limitations
The yields were moderate due to side reactions, and the relative configuration of the major adducts has not been unambiguously proven.
Digital Object Identifier (DOI)
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