| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344136 | Tetrahedron: Asymmetry | 2012 | 5 Pages |
(R)-(+)-Limonene was transformed into mono-N-tosylated-1,2-diamine derivatives using an N-tosylaziridination procedure followed by sodium azide treatment and reduction on Pd/C. The ligands obtained proved effective in the asymmetric transfer hydrogenation protocol on aromatic ketones.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(1S,2S,4R)-N-(2-Azido-4-isopropenyl-1-methyl-cyclohexyl)-4-methyl-benzenesulfonamideC17H24N4O2S[α]D23=+4.9 (c 1, CHCl3)Source of chirality: (R)-(+)-limoneneAbsolute configuration: (1S,2S,4R)
(1R,2R,5R)-N-(2-Azido-5-isopropenyl-2-methyl-cyclohexyl)-4-methyl-benzenesulfonamideC17H24N4O2S[α]D23=-54.0 (c 1, CHCl3)Source of chirality: (R)-(+)-limoneneAbsolute configuration: (1R,2R,5R)
(1S,2S,4R)-N-(2-Amino-4-isopropyl-1-methyl-cyclohexyl)-4-methyl-benzenesulfonamideC17H28N2O2S[α]D23=+18.6 (c 1, CHCl3)Source of chirality: (R)-(+)-limoneneAbsolute configuration: (1S,2S,4R)
(1R,2R,5R)-N-(2-Amino-5-isopropyl-2-methyl-cyclohexyl)-4-methyl-benzenesulfonamideC17H28N2O2S[α]D23=-10.4 (c 1, CHCl3)Source of chirality: (R)-(+)-limoneneAbsolute configuration: (1R,2R,5R)
