We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of Tetrasubstituted Nitroalkenes and Preliminary Studies of Their Enantioselective Organocatalytic Reduction.
- Authors
González, Patricia Camarero; Rossi, Sergio; Sanz, Miguel; Vasile, Francesca; Benaglia, Maurizio
- Abstract
Starting from commercially available ketones, a reproducible and reliable strategy for the synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure; the HWE olefination of the ketone to form the corresponding α,β-unsaturated esters is followed by a nitration reaction to introduce the nitro group in the α position of the ester group. The enantioselective organocatalytic reduction of these compounds has also been preliminarily studied, to access the functionalized enantioenriched nitroalkanes, which are useful starting materials for further synthetic elaborations. The absolute configuration of the reduction product was established by chemical correlation of the chiral nitroalkane with a known product; preliminary DFT calculations were also conducted to rationalize the stereochemical outcome of the organocatalytic enantioselective reduction.
- Subjects
KETONES; GROUP 15 elements; NITROALKANES; NITROALKENES; NITRATION; ESTERS
- Publication
Molecules, 2023, Vol 28, Issue 7, p3156
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28073156