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Chiral Phosphoric Acid Catalyzed Conversion of Epoxides into Thiiranes: Mechanism, Stereochemical Model, and New Catalyst Design.
- Source :
-
Angewandte Chemie . 2/21/2022, Vol. 134 Issue 9, p1-7. 7p. - Publication Year :
- 2022
-
Abstract
- Computations and experiments leading to new chiral phosphoric acids (CPAs) for epoxide thionations are reported. Density functional theory calculations reveal the mechanism and origin of the enantioselectivity of such CPA‐catalyzed epoxide thionations. The calculated mechanistic information was used to design new efficient CPAs that were tested experimentally and found to be highly effective. Bulky ortho‐substituents on the 3,3′‐aryl groups of the CPA are important to restrict the position of the epoxide in the key transition states for the enantioselectivity‐determining step. Larger para‐substituents significantly improve the enantioselectivity of the reaction. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PHOSPHORIC acid
*EPOXY compounds
*DENSITY functional theory
*SULFURATION
*CATALYSTS
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 134
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 155284188
- Full Text :
- https://doi.org/10.1002/ange.202113204