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Merging Ring-Opening 1,2-Metallate Shift with Asymmetric C(sp3)–H Borylation of Aziridines
- Source :
- Journal of the American Chemical Society; 20240101, Issue: Preprints
- Publication Year :
- 2024
-
Abstract
- Chiral secondary alkyl amines with a vicinal quaternary stereocenter are undoubtedly important and ubiquitous subunits in natural products and pharmaceuticals. However, their asymmetric synthesis remains a formidable challenge. Herein, we merge the ring-opening 1,2-metallate shift with iridium-catalyzed enantioselective C(sp3)–H borylation of aziridines to deliver these frameworks with high enantioselectivities. We also demonstrated the synthetic application by downstream transformations, including the total synthesis of two Amaryllidaceae alkaloids, (−)-crinane and (+)-mesmebrane.
Details
- Language :
- English
- ISSN :
- 00027863 and 15205126
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Periodical
- Accession number :
- ejs66842576
- Full Text :
- https://doi.org/10.1021/jacs.4c06569