6850-39-1Relevant academic research and scientific papers
Diastereoisomeric salt formation and enzyme-catalyzed kinetic resolution as complementary methods for the chiral separation of cis-/trans-enantiomers of 3-aminocyclohexanol
Brocklehurst, Cara E.,Laumen, Kurt,La Vecchia, Luigi,Voegtle, Markus,Shaw, Duncan
experimental part, p. 294 - 300 (2011/10/02)
This contribution demonstrates the preparative-scale synthesis of (1S,3S)-3-aminocyclohexanol by either enzymatic kinetic resolution of Cbz-protected 3-aminocyclohexanols or direct diastereoisomeric salt formation with (R)-mandelic acid. The salt formation demonstrates how a single enantiomer, (1S,3S)-3-aminocyclohexanol (R)-mandelate, can be effectively isolated from the cis/trans racemic mixture and subsequently converted to the free amine, (1S,3S)-3-aminocyclohexanol, by ion-exchange chromatography. We have also demonstrated how the other three enantiomers of 3-aminocyclohexanol can be prepared by either diastereoisomeric salt formation or enzymatic kinetic resolution.
Resolution of N-protected cis- and trans-3-aminocyclohexanols via lipase-catalyzed enantioselective acylation in organic media
Levy, Laura M.,De Gonzalo, Gonzalo,Gotor, Vicente
, p. 2051 - 2056 (2007/10/03)
The enzymatic acylation of N-protected cis-and trans-1,3-aminocyclohexanols using lipases in organic solvents is described. By modifying certain reaction parameters such as the solvent, the lipase and the N-protecting group, it is possible to achieve high enantioselectivities and to obtain enantiomerically pure 3-aminocyclohexanols. The influence of the N-protecting group and the conformation of the substrate on the reaction rate was also studied.
Resolution of trans-3-aminocyclohexanol
Bernardelli, Patrick,Bladon, Michael,Lorthiois, Edwige,Manage, Ajith C.,Vergne, Fabrice,Wrigglesworth, Roger
, p. 1451 - 1455 (2007/10/03)
(R,R)- and (S,S)-trans-3-Aminocyclohexanol were prepared via an enzymatic resolution of (±)-trans-1-acetoxy-3-benzylamido-cyclohexane with >95% enantiomeric excess.
Reactions of 1-acylamino-1-(trimethylsiloxy)alkanes: Versatile precursors to acylimines
Johnson, A. Peter,Luke, Richard W. A.,Boa, Andrew N.
, p. 895 - 905 (2007/10/03)
1-Acylamino-1-(trimethylsiloxy)alkanes react with carbon and heteroatom nucleophiles to give the corresponding 1-substituted-1-acylaminoalkanes. The 1-acylamino-1-(trimethylsiloxy)alkanes can also give rise to enamides, and by this route the mild antibiotic tuberin, and the isomeric (Z)-tuberin have been prepared. A further example of their reactions is illustrated with the acid-catalysed intramolecular cyclisation onto a carbon-carbon double bond. These transformations show that 1-acylamino-1-(trimethylsiloxy)alkanes are versatile precursors to synthetically useful acylimines.
Convenient Procedure for the Reduction of β-Enamino Ketones: Synthesis of γ-Amino Alcohols and Tetrahydro-1,3-oxazines
Bartoli, Giuseppe,Cimarelli, Cristina,Palmieri, Gianni
, p. 537 - 544 (2007/10/02)
γ-Amino alcohols 3 can be easily synthesized in very good yields by reduction of enaminones 1 with Na in PrOH-tetrahydrofuran.The reaction is fast, easy to perform, inexpensive and the easily accesible starting materials provide a convenient entry to γ-amino alcohols.The relative configuration assignment of the diastereomeric γ-amino alcohols obtained has been established by 1H and 13C NMR studies and unequivocally assigned by their cyclic tetrahydro-1,3-oxazine derivatives 4.
