Preparation of trans-1,2-diamino-1,2-dimethylcyclohexane via highly stereoselective olefin oxidation by dinitrogen tetroxide
Graphic
References (13)
- et al.
J. Am. Chem. Soc.
(1989)et al.J. Am. Chem. Soc.
(1990)et al.Chem. Lett.
(1986)et al.J. Am. Chem. Soc.
(1990)et al.J. Am. Chem. Soc.
(1987)et al.J. Org. Chem.
(1989)et al.J. Am. Chem. Soc.
(1989)et al. et al.J. Am. Chem. Soc.
(1989)et al.J. Org. Chem.
(1989) - et al.
J. Am. Chem. Soc.
(1984)et al.Tetrahedron Lett.
(1986)et al.Chem. Lett.
(1987)et al.Chem. Lett.
(1986) - et al.
Org. React.
(1946)Org. React.
(1946)Org. React.
(1946) - et al.
J. Am. Chem. Soc.
(1977)et al.Organometallics
(1983)Tetrahedron Lett.
(1978) - et al.
J. Am. Chem. Soc.
(1983)et al.Tetrahedron Lett.
(1984)et al.J. Org. Chem.
(1985)et al.Tetrahedron Lett.
(1986)
Cited by (24)
Methods for direct alkene diamination, new & old
2012, TetrahedronCitation Excerpt :The formation of trans imidazolines in this case corresponds to a cis-diamination process. Li has also discovered a number of other catalysts that significantly accelerate the imidazolination process, including Rh2TFA4·PPh3,145 FeCl3·PPh3,146 MnO2,147 and most recently, triphenylphosphine.148 In the case of MnO2 and Rh2TFA4·PPh3, diamination proceeds to generate the trichloromethyl rather than dichloromethyl imidazolines.
Advances in the application of N<inf>2</inf>O<inf>4</inf>/NO<inf>2</inf> in organic reactions
2010, TetrahedronCitation Excerpt :Catalytic hydrogenation of the produced compound with Pd(OH)2 on carbon affords a quantitative yield of (d,l)-1,2-diamino-1,2-dimethylcyclohexane 96. The latter is resolved into pure enantiomers via co-recrystallisation with mandelic acid (Scheme 30).186 The stereoselectivity may be rationalised with the help of Shechter’s proposed free-radical addition mechanism of N2O4 to alkenes, with a free and relatively long-lived tertiary radical 94 undergoing the less hindered axial attack by NO2 to afford 95 (Scheme 30).177
Salen ligands derived from trans-1,2-dimethyl-1,2-cyclohexanediamine: Preparation and application in oxo-chromium salen mediated asymmetric epoxidation of alkenes
2005, Journal of Molecular Catalysis A: ChemicalA new and facile route for the synthesis of chiral 1,2-diamines and 2,3-diamino acids
2005, Tetrahedron LettersAerobic, enantioselective epoxidation of non-functionalized olefins catalyzed by Ni(III) chiral Schiff base complexes
1998, Journal of Molecular Catalysis A: Chemical