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Synthesis 2015; 47(04): 569-574
DOI: 10.1055/s-0034-1378942
DOI: 10.1055/s-0034-1378942
paper
Novel (+)-3-Carene Derivatives and Their Application in Asymmetric Synthesis
Further Information
Publication History
Received: 05 August 2014
Accepted after revision: 06 November 2014
Publication Date:
03 December 2014 (online)
Abstract
A simple synthetic procedure for the preparation of mono-N-tosylated-1,2-diamines derived from (+)-3-carene is described. (+)-3-Carene is transformed into the corresponding N-tosylaziridine derivative using chloramine-T trihydrate. Subsequent ring opening with sodium azide followed by reduction of the azide function gives the optically pure mono-N-tosylated-1,2-diamine. This ligand is effective in asymmetric transfer hydrogenations of aromatic ketones. It can also be transformed into other chiral ligands by alkylation of the amino group for application in the addition of diethylzinc to benzaldehydes.
Key words
asymmetric catalysis - chiral auxiliaries - hydrogen transfer - ligands - natural productsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378942.
- Supporting Information
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