204275-02-5Relevant academic research and scientific papers
Asymmetric desymmetrization of a pseudo-meso endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one by chiral amines
Bakkeren, Frank J. A. D.,Ramesh, Namakkal G.,De Groot, Debby,Klunder, Antonius J. H.,Zwanenburg, Binne
, p. 8003 - 8006 (1996)
A novel route to the enantiopure endo-tricyclodecadienone system has been realized starting from the readily accessible pseudo-meso-5-hydroxy-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one 4. Dynamic kinetic resolution of (±)-4 using (S)-prolinol or its methyl ether leads to the corresponding enaminones 6b,c in high yields and with a de of 50%. Complete separation of the diastereomers of 6b is conveniently accomplished via their acetates. The absolute stereochemistry of the major diastereomer was shown to be ent-6b. Reductive elimination of the chiral auxiliary in ent-6b with lithium aluminum hydride affords optically pure parent tricyclodecadienone (+)-1 (X=H) in good overall yield.
Asymmetric desymmetrization of pseudo-meso 5-hydroxy-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-ones
Ramesh, Namakkal G,Bakkeren, Frank J.A.D,Groot, Debby De,Passamonti, Umberto,Klunder, Antonius J.H,Zwanenburg, Binne
, p. 9877 - 9887 (2007/10/03)
A novel route to the enantiopure endo-tricyclodecadienone system has been accomplished starting from readily accessible pseudo-meso-5-hydroxy-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3- one. Desymmetrization using (S)-prolinol or its methyl ether leads to the corresponding enaminones in high yields and with a de of 50%. Complete separation of the diastereomers has been conveniently achieved via their acetates. The absolute stereochemistry of the major diastereomer was determined by single-crystal X-ray diffraction analysis. Reductive elimination of the chiral auxiliary with lithium aluminum hydride affords optically pure parent tricyclodecadienone in good overall yield.
Molecular structure and absolute configuration of (+)-(1R, 2S, 6R, 7S, 1′R)-5-(1′-phenylethylamino)-endo-tricyclo[5.2.1.0 2,6]deca-4,8-dien-3-one
De Gelder, Rene,Smits, Jan M. M.,Ramesh, Namakkal G.,Bakkeren, Frank J. A. D.,De Groot, Debby,Klunder, Antonius J. H.
, p. 497 - 499 (2007/10/03)
The crystal and molecular structure of (+)-(1R, 2S, 6R, 7S, 1′R)-5-(1′-phenylethylamino)-endo-tricyclo[5.2.1.0 2,6]deca-4,8-dien-3-one is described. Based on the known absolute configuration (R) of the α-phenylethylamine moiety the X-ray analysis revealed the absolute configuration of the title compound. The structure was refined to R1 = 0.0298 for 1950 reflections (with I > 2σ(I)). Crystal data: C18H19NO, monoclinic, space group P21, a = 6.7406(4), b = 9.959(2), c = 11.3123(8)Ae, β = 102.969(5), V = 740.0(2)A3, and Z = 2.
