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Pseudo-Diastereodivergent Synthesis of Chiral Fluorenes Bearing Bis-1,3-Nonadjacent Stereogenic Centers via Organocatalytic Desymmetrization of meso-Epoxides
- Source :
- Organic Letters; 20230101, Issue: Preprints
- Publication Year :
- 2023
-
Abstract
- We report an enantio- and diastereodivergent synthesis of enantioenriched fluorenes bearing bis-1,3-nonadjacent stereocenters with broad substrate scope and high enantioselectivity (up to 99% ee) under low catalyst loading (0.1 mol %). The key to the success of this method is the pseudo-diastereodivergent desymmetrization of stereoisomers of meso-epoxides enabled by the same organocatalyst. Furthermore, some of the chiral fluorenes obtained exhibit high fluorescence quantum yields (up to 76.6%), as evidenced by photophysical properties studies.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs63662678
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c02150