Huang, X; De Haro, T; Nevado, C (2009). Gold-catalyzed stereocontrolled synthesis of 2,3-bis(acetoxy)-1,3-dienes. Chemistry - A European Journal, 15(24):5904-5908.
Change the ligand, change the stereochemistry: 2,3-Bis(acetoxy)-1,3-dienes are obtained in a stereocontrolled manner by a novel tandem 1,2-/1,2-bis(acetoxy) rearrangement (see scheme, R1 and R2 are + stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N-heterocyclic carbenes (NHC) favor cis alkenes, whereas phosphine ligands selectively afford trans olefins.
Change the ligand, change the stereochemistry: 2,3-Bis(acetoxy)-1,3-dienes are obtained in a stereocontrolled manner by a novel tandem 1,2-/1,2-bis(acetoxy) rearrangement (see scheme, R1 and R2 are + stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N-heterocyclic carbenes (NHC) favor cis alkenes, whereas phosphine ligands selectively afford trans olefins.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Language: | English |
| Date: | 2009 |
| Deposited On: | 15 Jan 2010 10:22 |
| Last Modified: | 17 Feb 2018 23:26 |
| Publisher: | Wiley-Blackwell |
| ISSN: | 0947-6539 |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1002/chem.200900391 |
Huang, X