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Synthesis of S(IV)‐Stereogenic Chiral Thio‐Oxazolidinones via Palladium‐Catalyzed Asymmetric [3+2] Annulations.
- Source :
- Angewandte Chemie; Mar2024, Vol. 136 Issue 13, p1-7, 7p
- Publication Year :
- 2024
-
Abstract
- Organic molecules bearing chiral sulfur stereocenters exert a great impact on asymmetric catalysis and synthesis, chiral drugs, and chiral materials. Compared with acyclic ones, the catalytic asymmetric synthesis of thio‐heterocycles has largely lagged behind due to the lack of efficient synthetic strategies. Here we establish the first modular platform to access chiral thio‐oxazolidinones via Pd‐catalyzed asymmetric [3+2] annulations of vinylethylene carbonates with sulfinylanilines. This protocol is featured by readily available starting materials, and high enantio‐ and diastereoselectivity. In particular, an unusual effect of a non‐chiral supporting ligand on the diastereoselectivity was observed. Possible reaction mechanisms and stereocontrol models were proposed. [ABSTRACT FROM AUTHOR]
- Subjects :
- ANNULATION
CHIRAL drugs
ASYMMETRIC synthesis
SULFUR
MOLECULES
HYDROGEN bonding
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 136
- Issue :
- 13
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 176104743
- Full Text :
- https://doi.org/10.1002/ange.202319728