Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis
Quoc Hoang Pham1, Christopher J T Hyland, Stephen G Pyne
1School of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong, Wollongong, New South Wales 2522, Australia. qhp428@uowmail.edu.au chrhyl@uow.edu.au spyne@uow.edu.au.
Organic & Biomolecular Chemistry
|September 15, 2020
Summary
Five-membered ring cyclic sulfamidate imines are versatile precursors for stereoselective heterocycle synthesis. Their reactivity as both electrophiles and nucleophiles enables the creation of complex, functionalized cyclic sulfamidates.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Five-membered ring cyclic sulfamidate imines (5H-1,2,3-oxathiazole 2,2-dioxides) are gaining prominence.
- These compounds feature a reactive N-sulfonyl imine within a stereodefined framework.
Purpose of the Study:
- To review recent advancements in the synthesis and reactivity of cyclic sulfamidate imines.
- To emphasize their utility in stereoselective synthetic processes.
Main Methods:
- Utilizing cyclic sulfamidate imines as substrates in nucleophilic additions and reductions.
- Exploiting the acidic protons adjacent to the imine moiety for nucleophilic participation.
Main Results:
- Demonstrated preparation of highly functionalized cyclic sulfamidates.
- Showcased the dual reactivity of cyclic sulfamidate imines as electrophiles and nucleophiles.
Conclusions:
- Cyclic sulfamidate imines are valuable building blocks for stereoselective synthesis.
- Their diverse reactivity facilitates the construction of complex heterocyclic structures.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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