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Synlett 2014; 25(4): 591-595
DOI: 10.1055/s-0033-1340471
DOI: 10.1055/s-0033-1340471
letter
Synthetic and Mechanistic Aspects on the Competition between C–H Insertion and Hydride Transfer in Copper-Mediated Transformations of α-Diazo-β-Keto Sulfones
Weitere Informationen
Publikationsverlauf
Received: 06. November 2013
Accepted: 23. November 2013
Publikationsdatum:
08. Januar 2014 (online)
Abstract
Competition between C–H insertion and hydride transfer is reported for the copper-catalysed reactions of a range of phenyl-substituted α-diazo-β-keto sulfones. Control of chemoselectivity is possible by alteration of the electronic properties of the diazo substrate. The production of enantioenriched cyclopentanones (up to 89% ee), formed via C–H insertion, and alkylidene tetrahydrofurans (up to 43% ee), produced via hydride transfer, is described. The isolation of products derived from hydride transfer provides mechanistic insight into the copper-mediated C–H insertion of α-diazocarbonyl compounds.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synlett and can be cited using the following DOI: 10.4125/pd0054th.
- Primary Data
-
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