| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347203 | Tetrahedron: Asymmetry | 2009 | 6 Pages |
The regio- and stereoselective osmium-catalysed aminohydroxylation of (+)-2-carene (99% ee), and (+)-3-carene (99% ee), (−)-β-pinene (99% ee) and (−)-camphene (75% ee) with chloramine-T is described. The products β-hydroxy-p-toluenesulfonamides were reduced with sodium in liquid ammonia to give the corresponding β-amino alcohols with 48–83% yields. The methylation-reduction of β-hydroxy-p-toluenesulfonamides gave β-methylamino alcohols with 33–55% yields.
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N-((1R,3R,4S,6S)-(+)-4-Hydroxy-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-yl)-4-methylbenzenesulfonamideC17H25NO3SEe = 99%[α]D20=+34.5 (c 1.5, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1R,3R,4S,6S)
(1S,3S,4R,6R)-(+)-4-Amino-3,7,7-trimethyl-bicyclo[4.1.0]heptan-3-olC10H19NOEe = 99%[α]D20=+12.5 (c 3.2, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1S,3S,4R,6R)
N-((1R,3R,4S,6S)-(+)-4-Hydroxy-4,7,7-trimethylbicyclo-[4.1.0]heptan-3-yl)-N-4-dimethylbenzenesulfonamideC18H27NO3SEe = 99%[α]D20=+64.5 (c 2.0, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1R,3R,4S,6S)
(1S,3S,4R,6R)- 3,7,7-Trimethyl-4-(methylamino)bicyclo-[4.1.0]heptan-3-olC11H21NOEe = 99%[α]D20=-29.9 (c 2.5, CHCl3)Source of chirality: (+)-3-careneAbsolute configuration: (1S,3S,4R,6R)
N-((1S,2S,3R,6R)-(+)-3-Hydroxy-3,7,7-trimethylbicyclo-[4.1.0]heptan-2-yl)-4-methylbenzenesulfonamideC17H25NO3SEe = 99%[α]D20=+48.7 (c 1.5, CHCl3)Source of chirality: (+)-2-careneAbsolute configuration: (1S,2S,3R,6R)
(1S,2S,3R,6R)-(–)-2-Amino-3,7,7-trimethylbicyclo[4.1.0]heptan-3-olC10H19NOEe = 99%[α]D20=-8.4 (c 2.7, CHCl3)Source of chirality: (+)-2-careneAbsolute configuration: (1S,2S,3R,6R)
N-((1S,2S,3R,6R)-3-Hydroxy-3,7,7-trimethylbicyclo[4.1.0]heptan-2-yl)-N-4-dimethylbenzenesulfonamideC18H27NO3SEe = 99%[α]D20=-51.0 (c 1.45, CHCl3)Source of chirality: (+)-2-careneAbsolute configuration: (1S,2S,3R,6R)
(1S,2S,3R,6R)-3,7,7-Trimethyl-2-(methylamino)bicyclo-[4.1.0]heptan-3-olC11H21NOEe = 99%[α]D20=+36.4 (c 2.15, CHCl3)Source of chirality: (+)-2-careneAbsolute configuration: (1S,2S,3R,6R)
N-(((1R,2S,5S)-(–)-2-Hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl)-4-methylbenzenesulfonamideC17H25NO3SEe = 99%[α]D20=-19.0 (c 1.5, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1R,2S,5S)
(1R,2S,5S)-(–)-2-(Aminomethyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-olC10H19NOEe = 99%[α]D20=-51.3 (c 2.6, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1R,2S,5S)
N-(((1R,2S,5S)-2-Hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethyl)-N-4-dimethylbenzenesulfonamideC18H27NO3SEe = 99%[α]D20=-16.5 (c 3.5, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1R,2S,5S)
(1R,2S,5S)-6,6-Dimethyl-2-((methylamino)methyl)bicyclo-[3.1.1]heptan-2-olC11H21NOEe = 99%[α]D20=-60.0 (c 1.15, CHCl3)Source of chirality: (−)-β-pineneAbsolute configuration: (1R,2S,5S)
N-(((1R,2R,4S)-2-Hydroxy-3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)-4-methylbenzenesulfonamideC17H25NO3SEe = 75%[α]D20=+14.2 (c 1.25, CHCl3)Source of chirality: (−)-campheneAbsolute configuration: (1R,2R,4S)
(1R,2R,4S)-2-(Aminomethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-olC10H19NOEe = 75%[α]D20=+18.7 (c 1.1, DMSO)Source of chirality: (−)-campheneAbsolute configuration: (1R,2R,4S)
N-(((1R,2R,4S)-2-Hydroxy-3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)-N-4-dimethylbenzenesulfonamideC18H27NO3Ee = 75%[α]D20=+1.4 (c 2.2, DMSO)Source of chirality: (−)-campheneAbsolute configuration: (1R,2S,4S)
(1R,2R,4S)-3,3-Dimethyl-2-((methylamino)methyl)bicyclo-[2.2.1]heptan-2-olC11H21NOEe = 75%[α]D20=+18.2 (c 1.35, MeOH)Source of chirality: (−)-campheneAbsolute configuration: (1R,2R,4S)
