Structure-chiroptical properties relationship of cisoid enones with an α-methylenecyclopentanone unit

RSC Advances

Volumn 4, Issue 83, 2014, Pages 43977-43993

  Frelek, Jadwiga ^a   Butkiewicz, Aleksandra ^a   Górecki, Marcin ^a   Wojcieszczyk, Ryszard K ^b   Luboradzki, Roman ^c   Kwit, Marcin ^d   Rode, Michał F ^e   Szczepek, Wojciech J ^f  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b KAZIMIERZ PULASKI UNIVERSITY OF TECHNOLOGY AND HUMANITIES IN RADOM   (Poland)

^c INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^d ADAM MICKIEWICZ UNIVERSITY   (Poland)

^e INSTITUTE OF PHYSICS   (Poland)

^f INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84907611569     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra04991h     Document Type: Article

References (46)

1. S. F. Brady M. P. Singh J. E. Janso J. Clardy J. Am. Chem. Soc. 2000 122 2116 2117
2. F. Grundschober Perfum. Flavor. 1979 4 15 17
3. M. Mikołajczyk P. Bałczewski Tetrahedron 1989 45 7023 7030
4. M. P. Singh J. E. Janso S. W. Luckman S. F. Brady J. Clardy M. Greenstein W. M. Maiese J. Antibiot. 2000 53 256 261
5. M. Kettering C. Valdivia O. Sterner H. Anke E. Thines J. Antibiot. 2005 58 390 396
6. C. Valdivia M. Kettering H. Anke E. Thines O. Sterner Tetrahedron 2005 61 9527 9531
7. D. N. Kirk Tetrahedron 1986 42 777 818
8. C. Djerassi R. Records E. Bunnenberg K. Mislow A. Moscowitz J. Am. Chem. Soc. 1962 84 870 872
9. G. Snatzke Tetrahedron 1965 21 413 419
10. G. Snatzke Tetrahedron 1965 21 421 438
11. G. Snatzke Tetrahedron 1965 21 439 448
12. W. B. Whalley Chem. Ind. 1962 1024 1027
13. G. Snatzke, in Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, ed., G. Snatzke, Sadtler Research Labs Inc., Philadelphia, 1967, pp. 208-223
14. G. Snatzke Angew. Chem., Int. Ed. Engl. 1979 18 363 377
15. J. K. Gawroński Tetrahedron 1982 38 3 26
16. J. Frelek W. J. Szczepek H. P. Weiss Tetrahedron: Asymmetry 1993 4 411 424
17. N. Purdie and H. G. Brittain, Analytical application of circular dichroism, in Techniques and Instrumentation in Analytical Chemistry, Elsevier, Amsterdam-London-New York-Tokyo, 1994, vol. 14
18. J. K. Gawroński, Conformations, Chiroptical and Related Spectral Properties of Enones, in The Chemistry of Enones, ed., S. Patai, and, Z. Rappoport, John Wiley & Sons Ltd, New York, 1989, pp. 55-105
19. D. A. Lightner and J. E. Gurst, Organic Conformational Analysis and Stereochemistry from Circular Dichroism Spectroscopy, Wiley-VCH, New York, 2000
20. N. Berova, K. Nakanishi and R. W. Woody, Circular Dichroism: Principles and Applications, Wiley-VCH, New York, 2nd edn, 2000
21. E. Orentas G. Bagdziunas U. Berg A. Zilinskas E. Butkus Eur. J. Org. Chem. 2007 4251 4256
22. M. Kwit, P. Skowronek, J. Gawroński, J. Frelek, M. Woźnica and A. Butkiewicz, Some inherently chiral chromophores-empirical rules and quantum chemical calculations, in Comprehensive Chiroptical Spectroscopy, ed., N. Berova, P. L. Polavarapu, K. Nakanishi, and, R. W. Woody, John Wiley and Sons, Inc, Hoboken, New Jersey, 2012, vol. 2, pp. 39-72
23. G. Snatzke, in Fundamental aspects and recent developments in optical rotatory dispersion and circular dichroism, ed., F. Ciardelli, and, P. Salvadori, Heyden, London, 1973, pp. 109-124
24. J. Frelek W. J. Szczepek H. P. Weiss Tetrahedron: Asymmetry 1995 6 1419 1430
25. G. Ruecker K. H. Kahrs H.-W. Hembeck Arch. Pharm. 1975 308 858 862
26. J. Frelek W. J. Szczepek H. P. Weiss G. J. Reiss W. Frank J. Brechtel B. Schulthesis H.-G. Kuball J. Am. Chem. Soc. 1998 120 7010 7019
27. D. A. Lightner M. J. Flores B. Vincent Crist J. K. Gawroński J. Org. Chem. 1980 45 3518 3522
28. E. C. Taylor Y. Shvo J. Org. Chem. 1968 33 1719 1727
29. S. J. DeSolms J. Org. Chem. 1976 41 2650 2651
30. T. Bakos I. Vincze Synth. Commun. 1992 22 1377 1383
31. D. N. Kirk V. Petrow M. Stansfield D. M. Williamson J. Chem. Soc. 1960 2385 2388
32. J. Gawroński A. Gałat Rocz. Chem. 1975 49 91 97
33. C. W. Shoppee G. H. R. Summers J. Chem. Soc. 1952 2528 2530
34. R. M. Moriarty E. S. Wallis J. Org. Chem. 1959 24 1274 1278
35. L. F. Fieser G. Ourisson J. Am. Chem. Soc. 1953 75 4404 4414
36. M. Anastasia A. Fiecchi A. Scala J. Chem. Soc., Perkin Trans. 1 1979 1821 1824
37. L. F. Fieser J. E. Herz J. Am. Chem. Soc. 1953 75 121 124
38. O. Wintersteiner M. Moore J. Am. Chem. Soc. 1943 65 1507 1512
39. O. Wintersteiner M. Moore J. Am. Chem. Soc. 1943 65 1513 1516
40. M. Kwit J. Gawroński D. R. Boyd N. D. Sharma M. Kaik Org. Biomol. Chem. 2010 8 5635 5645
41. HyperChem(TM) Professional 8.0, Hypercube, Inc., Gainesville, FL
42. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010
43. G. Scalmani M. J. Frisch J. Chem. Phys. 2010 132 114110
44. J. K. Gawroński, Konformacja i czynnos̈ć optyczna cyklicznych α,β-nienasyconych ketonów, Wydawnictwo Naukowe UAM, Seria Chemia No. 21, Poznań, 1976, p. 94
45. A. W. Burgstahler R. C. Barkhurst J. Am. Chem. Soc. 1970 92 7601 7603
46. A. F. Beecham Tetrahedron 1971 27 5207 5216