Abstract
An unusual room temperature β-lactone decarboxylation facilitated a five-step enantioselective formal synthesis of the cyclopentane core of an estrogen receptor β-agonist. A computational study probed the underlying factors facilitating unprecedented, rapid decarboxylation. Aryl substitution promotes faster reaction in the retro-[2+2] as a result of conjugative stabilization with the forming olefin. Additionally, the configuration of the α-ester in these fused β-lactones leads to differential decarboxylation rates.
Original language | English (US) |
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Pages (from-to) | 2690-2693 |
Number of pages | 4 |
Journal | Chemical Communications |
Volume | 51 |
Issue number | 13 |
DOIs | |
State | Published - Feb 14 2015 |
ASJC Scopus subject areas
- Electronic, Optical and Magnetic Materials
- General Chemistry
- Ceramics and Composites
- Metals and Alloys
- Materials Chemistry
- Surfaces, Coatings and Films
- Catalysis