Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems.
| Autor: | Augustin AU; Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 3200009, Israel., Di Silvio S; Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 3200009, Israel., Marek I; Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 3200009, Israel. |
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| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2022 Sep 14; Vol. 144 (36), pp. 16298-16302. Date of Electronic Publication: 2022 Aug 30. |
| DOI: | 10.1021/jacs.2c07394 |
| Abstrakt: | Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivered the title compounds. |
| Databáze: | MEDLINE |
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