Publication: Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural
All || By Area || By Year| Title | Inverse Temperature Dependence in the Diastereoselective Addition of Grignard Reagents to a Tetrahydrofurfural | Authors/Editors* | J. Mowat, B. Kang, B. Fonovic, T. Dudding, R. Britton |
|---|---|
| Where published* | Organic Letters |
| How published* | Journal |
| Year* | 2009 |
| Volume | 11 |
| Number | 10 |
| Pages | 2057-2060 |
| Publisher | American Chemical Society |
| Keywords | DFT, Grginard Reactivity, Inverse Temperature Dependence |
| Link | http://pubs.acs.org/doi/pdf/10.1021/ol900324s |
| Abstract |
A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer |
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