VCD configuration of enantiopure/-enriched tetrasubstituted α-fluoro cyclohexanones and their use for epoxidation of trans-olefins

Chirality

Volumn 16, Issue 7, 2004, Pages 467-474

  Freedman, T B ^a   Cao, X ^a   Nafie, L A ^a   Solladié Cavallo, Arlette ^b   Jierry, L ^b   Bouerat, L ^b  

^a SYRACUSE UNIVERSITY   (United States)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Asymmetric epoxidation; Chiral dioxiranes; DFT calculation; Solution conformation; Vibrational circular dichroism

Indexed keywords

ALKENE; ALPHA FLUOROCYCLOHEXANONE DERIVATIVE; BETA METHYLSYTRENE; CHLOROFORM; CINNAMIC ACID DERIVATIVE; CYCLOHEXANONE DERIVATIVE; DEUTERATED CHLOROFORM; DEUTERIUM; DIOXIRANE DERIVATIVE; ETHYLENE OXIDE; FLUORINE; KETONE; METHYL 4 METHOXYCINNAMATE; STILBENE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; CIRCULAR DICHROISM; COMPARATIVE STUDY; CONFORMATION; DENSITY FUNCTIONAL THEORY; DISSOLUTION; ENANTIOMER; ENERGY; EPOXIDATION; GAS; MOLECULAR STABILITY; PRIORITY JOURNAL; STEREOCHEMISTRY; VIBRATIONAL CIRCULAR DICHROISM;

EID: 3242681511     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20061     Document Type: Article

References (34)

1. Solladié-Cavallo A, Bouérat L. Epoxidation of p-methoxycinnamates using chiral dioxiranes derived from new trisubstituted halogenated cyclohexanones: enhanced efficiency of ketones having an axial halogen. Organ Lett 2000;2:3531-3534.
2. Solladié-Cavallo A, Bouérat L, Jierry L. Asymmetric epoxidation of trans-olefins via chiral dioxiranes: a possible contribution of axial approaches in the case of tri- and tetrasubstituted α-fluoro cyclohexanones. Eur J Org Chem 2001:4557-4560.
3. Baumstark AL, McCloskey CJ. Epoxidation of alkenes by dimethyl-dioxirane: evidence for a spiro transition state. Tetrahedron Lett 1987;28:3311-3314.
4. Adam W, Paredes R, Smerz AK, Veloza LA. Probing for steric and electronic effects in diastereoselective dioxirane epoxidations compared to the oxygen transfer by peroxy acids. Liebigs Annalen/Recueil 1997:547-551.
5. Houk KN, Liu J, DeMello NC, Condroski KR. Transition states of epoxidations: diradical character, spiro geometries, transition state flexibility, and the origins of stereoselectivity. J Am Chem Soc 1997;119:10147-10152.
6. Jenson C, Liu J, Houk KN, Jorgensen WL. Elucidation of transition structures and solvent effects for epoxidation by dimethyldioxirane. J Am Chem Soc 1997;119:12982-12983.
7. Bach RD, Andres JL, Owensby AL, Schlegel HB, McDouall JJW. Electronic structure and reactivity of dioxirane and carbonyl oxide. J Am Chem Soc 1992;114:7207-7217.
8. Armstrong A, Washington I, Houk KN. Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes. J Am Chem Soc 2000;122:6297-6298.
9. Solladié-Cavallo A, Jierry L, Bouerat L, Taillasson P. Tri- and tetra-substituted α-fluorocyclohexanones with enantiomerc excesses in the range of 97-100%. Tetrahedron: Asymmetry 2001;12:883-891.
10. FH. Tetrahedron 2002;58:4195-4199.
11. Imuta M, Ziffer H. Synthesis and physical properties of a series of optically active substituted trans-stilbene oxides. J Org Chem 1979;44:2505-2509.
12. Matsuki K, Sobukawa M, Kawai A, Inoue H, Takeda M. Asymmetric reduction of aromatic ketones. II. An enantioselective synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate. Chem Pharm Bull 1993;41:643-648.
13. Witkop B, Foltz CM. The stereochemistry of ephedrine and y-ephedrine. J Am Chem Soc 1957;79:197-201.
14. Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758.
15. Stephens PJ, Devlin FJ. Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 2000;12:172-179.
16. Solladié-Cavallo A, Balaz M, Salisova M, Suteu C, Nafie LA, Cao X, Freedman TB. A new chiral oxathiane: synthesis, resolution and absolute configuration determination by vibrational circular dichroism. Tetrahedron: Asymmetry 2001;12:2605-2611.
17. Solladié-Cavallo A, Sedy O, Salisova M, Biba M, Welch CJ, Nafie L, Freedman T. A chiral 1,4-oxazin-2-one: asymmetric synthesis versus resolution, structure, conformation and VCD absolute configuration. Tetrahedron: Asymmetry 2001;12:2703-2707.
18. Solladié-Cavallo A, Marsol C, Pescitelli G, Di Bari L, Salvadori P, Huang X, Fujioka N, Berova N, Cao X, Freedman TB, Nafie LA. (R)-(+)- and (S)-(-)-1-(9-phenanthryl)ethylamine: assignment of absolute configuration by CD tweezer and VCD methods, and difficulties encountered with the CD exciton chirality method. Eur J Org Chem 2002;1788-1796.
19. Dyatkin AB, Freedman TB, Cao X, Dukor RK, Maryanoff BE, Maryanoff CA, Matthews JM, Shah RD, Nafie LA. Determination of the absolute configuration of a key trcyclic component of a novel vasopressin receptor antagonist by use of vibrational circular dichroism. Chirality 2002;14:215-219.
20. Freedman TB, Dukor RK, van Hoof PJCM, Kellenbach ER, Nafie LA. Determination of the absolute configuration of (-)-mirtazapine by vibrational circular dichroism. Helv Chim Acta 2002;85:1160-1165.
21. 2-symmetric dimer of 1,1′-binaphthyl. J Phys Chem A 2003;107:7692-7696.
22. Freedman TB, Cao X, Nafie LA, Kalbermatter M, Linden A, Rippert AJ. An unexpected atropisomerically stable 1,1-biphenyl at ambient temperature in solution, elucidated by vibrational circular dichroism (VCD). Helv Chim Acta 2003;86:3141-3155.
23. Freedman TB, Cao X, Oliveira RV, Cass QB, Nafie LA. Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism. Chirality 2003;15:196-200.
24. Izumi H, Futamura S, Nafie LA, Dukor RK. Determination of molecular stereochemistry using vibrational circular dichroism spectroscopy: absolute configuration and solution conformation of 5-formyl-cis, cis-1,3,5-trimethyl-3- hydroxymethylcyclohexane-1-carboxylic acid lactone. Chem Rec 2003;3:112-119.
25. Maryanoff BE, McComsey DF, Dukor RK, Nafie LA, Freedman TB, Cao X, Day VW. Structural studies on McN-5652-X, a high-affinity ligand for the serotonin transporter in mammalian brain. Bioorg Med Chem 2003;11:2463-2470.
26. Monde K, Taniguchi T, Miura N, Nishimura S-I, Harada N, Dukor RK, Nafie LA. Preparation of cruciferous phytoalexin related metabolites, (-)-dioxibrassinin and (-)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD). Tetrahedron Lett 2003;44:6017-6020.
27. Solladié-Cavallo A, Marsol C, Yaakoub M, Azyat K, Klein A, Roje M, Suteu C, Freedman TB, Cao X, Nafie LA. Erythro-1-naphthyl-1-(2-piperidyl) methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration. J Org Chem 2003;68:7308-7315.
28. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98. A.9. Pittsburgh: Gaussian, Inc.; 1998.
29. Basso EA, Kaiser C, Rittner R, Lambert JB. Axial/equatorial proportions for 2-substituted cyclohexanones. J Org Chem 1993;58:7865-7869.
30. Pan Y-H, Strothers JB. Nuclear magnetic resonance studies. XIV. Conformational equilibria of α-halocyclohexanones. Can J Chem 1967;45:2943-2953.
31. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, J. A. Montgomery J, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03. Revision, B.03. Pittsburgh: Gaussian, Inc.; 2003.
32. Fortunelli A, Tomasi J. The implementation of density functional theory within the polarizable continuum model for solvation. Chem Phys Lett 1994:231:34-39.
33. Mennucci B, Cammi R, Tomasi J. Medium effects on the properties of chemical systems: electric and magnetic response of donor-acceptor systems within the polarizable continuum model. Int J Quant Chem 1999;75:767-781.
34. 4 solution. J Phys Chem A 2002;106:12331-12339.