Conformation and absolute configuration of 2-naphthylalkylsulfoxides by combined use of dynamic NMR, ECD spectroscopy, DFT computations, and x-ray diffraction

Chirality

Volumn 21, Issue 1, 2009, Pages 16-23

  Casarini, Daniele ^a   Lunazzi, Lodovico ^b   Mancinelli, Michele ^b   Mazzanti, Andrea ^b   Scafato, Patrizia ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Anomalous x ray dispersion; Circular dichroism; DFT calculations; Dynamic NMR; Enantioselective HPLC

Indexed keywords

2 NAPHTHYLALKYLSULFOXIDE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; ENANTIOMER; ENANTIOSELECTIVITY; FOURIER TRANSFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SEPARATION TECHNIQUE; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 60849107602     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20587     Document Type: Article

References (42)

1. Mislow K, Ternay AL Jr, Melillo JT. Cotton effect in optically active sulfoxides. J Am Chem Soc 1963;85:2329-2330.
2. Mislow K, Green MM, Laur P, Melillo JT, Simmons T, Ternay AL Jr. Absolute configuration and optical rotatory power of sulfoxides and sulfinate esters. J Am Chem Soc 1965;87:1958-1976.
3. Jacobus J, Mislow K. Racemization and cleavage of sulfoxides by methyllithium. J Am Chem Soc 1967;89:5228-5234.
4. Saeva FD, Rayner DR, Mislow K. Direct configurational correlation of sulfoxides and phosphine oxides by intersystem matching of Cotton effect. J Am Chem Soc 1968;90:4176-4168.
5. Landini D, Modena G, Montanari F, Scorrano G. Reduction and racemization of sulfoxides by halide ions in aqueous perchloric acid. J Am Chem Soc 1970;92:7168-7174.
6. Quintily U, Scorrano G. A novel method of measuring the protonation of sulfoxides. Chem Commun 1971:260-261.
7. Andersen KK. Stereochemistry, conformation, and chiroptical properties of sulfoxides. In:Patai S, Rappoport Z, Stirling CJM, editors. The chemistry of sulfones and sulfoxides. Chichester UK: Wiley; 1988 p 55-94.
8. Pitchen P, Duñach E, Deshmukh MN, Kagan HB. An efficient asymmetric oxidation of sulfides to sulfoxides. J Am Chem Soc 1984;106, 8188-8193.
9. Rebiere F, Samuel O, Ricard L, Kagan HB. A general route to enantiomerically pure sulfoxides from a chiral sulfate. J Org Chem 1991; 56:5991-5999.
10. Brunel J-M, Diter P, Dustch M, Kagan HB. Highly enantioselective oxidation of sulfides mediated by a chiral titanium complex. J Org Chem 1995;60:8086-8088.
11. Kagan HB. Asymmetric oxidation of sulfides. In: Ojima I, editor. Catalytic asymmetric synthesis. New York: VCH; 1993. p 203-226.
12. Andersen KK. Synthesis of (+)-ethyl p-tolyl sulfoxide from (-)-menthyl (-)-p-toluenesulfinate. Tetrahedron Lett 1962;3:93-95.
13. Di Furia F, Modena G, Seraglia R. Synthesis of chiral sulfoxides by metal-catalyzed oxidation with t-butyl hydroperoxide. Synthesis 1984:325-326.
14. Andersen KK, Gaffield W, Papanikolaou NE, Foley JW, Perkins RI. Optically active sulfoxides. The synthesis and rotatory dispersion of some diaryl sulfoxides. J Am Chem Soc 1964;86:5637-5646.
15. De Lucchi O, Lucchini V, Marchioro C, Valle G, Modena G. Self-induced diastereoselective oxidation of vinyl sulfoxides bearing a chiral hydroxy group as a way of preparation of optically active sulfinyl dienophiles and their use in the asymmetric Diels-Alder reactions to cyclopentadiene. J Org Chem 1986;51:1457-1466.
16. Di Furia F, Licini G, Modena G, Motterle R, Nugent WA. Enantioselective titanium catalyzed sulfides oxidation: novel ligands provide significantly improved catalyst life. J Org Chem 1996;61:5175-5177.
17. 2O/(R,R)-diphenylethane-1,2-diol complex: a versatile and highly enantioselective oxidation protocol. J Org Chem 1998;63:9392-9395.
18. Clayden J, Kubinski PM, Sammiceli F, Helliwell M, Diorazio L. Sulfoxides as 'traceless' resolving agents for the synthesis of atropisomers by dynamic or classical resolution. Tetrahedron 2004;60:4387-4397.
19. Casarini D, Lunazzi L, Gasparrini F, Villani C, Cirilli M, Gavuzzo E. Conformational assignment, absolute configuration, and chiral separation of all the stereoisomers created by the combined presence of stereogenic centers and stereogenic conformational axes in a highly hindered 1,5-naphthyl sulfoxide. J Org Chem 1995;60:97-102.
20. Casarini D, Lunazzi L, Mazzanti A, Mercandelli P, and Sironi A. Conformational studies by dynamic NMR. 99. Experimental and computed determination of rotation barriers in the crystalline state: the case of naphthylphenylsulfoxide. J Org Chem 2004;69:3574-3577.
21. Bendazzoli GL, Palmieri P, Gottarelli G, Moretti I, Torre G. A circular dichroism study of the first excited electronic state in propylene episulfoxide. J Am Chem Soc 1976;98:2659-2660.
22. Moretti I, Torre G, Gottarelli G. Circular dichroism of chiral episulphoxides. Tetrahedron Lett 1976;17:711-714.
23. Rosini C, Donnoli MI, Superchi S. Toward a correlation of absolute configuration and chiroptical properties of alkyl aryl sulfoxides: a couplet-oscillator foundation of the empirical Mislow rule. Chem Eur J 2001;7:72-79.
24. Donnoli MI, Giorgio E, Superchi S, Rosini C. Org Biomol Chem 2003;1:344-3449.
25. Donnoli MI, Superchi S, Rosini C. Recent progress in application of spectroscopic methods for assigning absolute configuration of optically active sulfoxides. Mini Rev Org Chem 2006;3:77-92.
26. Devlin FJ, Stephen PJ, Scafato P, Superchi S, Rosini C. Determination of absolute configuration using vibrational circular dichroism spectroscopy: the chiral sulfoxide 1-thiochroman S-oxide. Tetrahedron:Asymmetry 2001;12:1551-1558.
27. Stephens PJ, Aamouche A, Devlin FJ, Superchi S, Donnoli MI, Rosini C. Determination of absolute configuration using vibrational circular dichroism spectroscopy: the chiral sulfoxide 1-(2-methylnaphthyl) methylsulfoxide. J Org Chem 2001;66:3671-3677.
28. Berova N, Di Bari L, Pescitelli G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 2007;36:914-931.
29. Casarini D, Foresti E, Gasparrini F, Lunazzi L, Macciantelli D, Misiti D, Villani C. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics and chiral resolution. J Org Chem 1993;58:5674-5682.
30. Jennings WB, Kochanewycz MJ, Lunazzi L. Conformation and stereodynamics of alkyl 9-anthrylsulfoxides. J Chem Soc Perkin Trans 2 1997:2271-2273.
31. Casarini D, Grilli S, Lunazzi L, Mazzanti A. Conformational studies by dynamic NMR. 80. Cog-wheel effect in the stereolabile helical enantiomers of dimesityl sulfoxides and sulfone. J Org Chem 2001;66: 2757-2763.
32. Mc Killop A, Koyunçu D. Efficient high yield oxidation of thiols and selenols to disulphides and diselenides. Tetrahedron Lett 1990;31: 5007-5010.
33. Lupattelli P, Ruzziconi R, Scafato P, Degl'Innocenti A, Paolobelli AB. 1,1,1-Trifluoro-acetone as an efficient catalyst for the hydrogen peroxide promoted selective oxidation of sulfides to sulfoxides. Synth Commun 1997;27:441-446.
34. Bradley SA, Krishnamurthy K. A modified CRISIS-HSQC for band-selective IMPRESS. Magn Res Chem 2005;43:117-123.
35. Willker W, Leibfritz D, Kerssebaum R, Bermel W. Gradient selection in inverse heteronuclear correlation spectroscopy. Magn Res Chem 1993;31:287-292.
36. Hurd RE, John BK. Gradient-enhanced proton-detected heteronuclear multiple-quantum coherence spectroscopy. J Magn Reson 1991;91: 648-653.
37. Stott K, Stonehouse J, Keeler J, Hwand TL, Shaka AJ. Excitation sculpting in high-resolution nuclear magnetic resonance spectroscopy: application to selective NOE experiments J Am Chem Soc 1995;117: 4199-4200.
38. Kupče E, Boyd J, Campbell ID. Short selective pulses for biochemical applications. J Magn Reson Series B, 1995;106:300.
39. Brown JH, Bushweller CH. DNMR6: Calculation of NMR spectra subject to the effects of chemical exchange. QCPE Bull 1983;3: 103.
40. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, 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, Bakken V, 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 D.01. Wallingford CT: Gaussian, Inc.; 2004.
41. O'Boyle NM, Tenderholt AL, Langner KM. cclib: A library for package-independent computational chemistry algorithms. J Comp Chem 2008;29:839-845.
42. Jennings WB. Chemical shift nonequivalence in prochiral groups. Chem Rev 1975;75:307-322.