Abstract
We report a highly diastereoselective protocol for the synthesis of 1,4- and 1,5-dicarbonyl compounds from densely substituted cyclopropanols. The methodology involves a palladium-catalyzed ring opening reaction followed by a “metal-walk” and oxidation of a remote hydroxyl group. The methodology represents a new application of cyclopropanols as initiation sites for chain walking remote functionalization. Importantly, this approach provides a straightforward access to highly valuable succinaldehyde derivatives bearing vicinal quaternary and tertiary stereocenters as single diastereomers.
Original language | English |
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Journal | Angewandte Chemie - International Edition |
DOIs | |
State | Accepted/In press - 2024 |
Keywords
- chain walking
- cyclopropanols
- homoenolates
- palladium catalysis
- stereoselective synthesis
All Science Journal Classification (ASJC) codes
- Catalysis
- General Chemistry