Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones
Elżbieta Łastawiecka1, Sławomir Frynas1, K Michał Pietrusiewicz1
1Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sklodowska University, Gliniana 33 St., 20-614 Lublin, Poland.
The Journal of Organic Chemistry
|April 26, 2021
Summary
Novel synthetic methods create optically active P-stereogenic phosphin-en-ones. These efficient one-pot processes yield valuable enantiomerically enriched organophosphorus compounds.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Organophosphorus Chemistry
Background:
- 1-phenylphosphinan-4-ones are versatile precursors.
- Developing enantioselective routes to P-stereogenic compounds is crucial.
Purpose of the Study:
- To develop novel synthetic protocols for P-stereogenic 1-phenylphosphin-2-en-4-ones.
- To achieve high enantiomeric purity in the synthesized compounds.
Main Methods:
- Enantioselective deprotonation followed by oxidation.
- Asymmetric organocatalytic halogenation with elimination.
- Two-step one-pot transformations.
Main Results:
- Successful synthesis of optically active 1-phenylphosphin-2-en-4-one 1-sulfide and 1-oxide.
- Achieved 96% enantiomeric purity for the sulfide and 55% for the oxide.
- Demonstrated efficient one-pot access to target molecules.
Conclusions:
- Two new synthetic strategies provide access to valuable P-stereogenic organophosphorus compounds.
- The developed methods offer high enantioselectivity and efficiency.
- These protocols are significant for asymmetric synthesis in organophosphorus chemistry.
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