An interplay in the regioselectivity induced by non bonding interactions, in the ene reactions of singlet oxygen and triazolinediones with tetrasubstituted alkenes

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6437-6440

  Elemes, Yiannis ^a   Stratakis, Manolis ^b   Orfanopoulos, Michael ^c  

^a UNIVERSITY OF IOANNINA   (Greece)

^b UNIVERSITY OF CYPRUS   (Cyprus)

^c UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030793770     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01471-8     Document Type: Article

References (22)

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3. c) Frimmer, A. A.; Stephenson, L. M. Singlet oxygen, reactions, modes and products, A. A. Frimer Eds. CRC Press. Boca Raton FL. 1985 vol. II, Chapters, pp. 68-87.
4. d) Foote, C. S.; Clennan, E. L. in Active Oxygen in Chemistry; Foote, C. S.; Valentine, J. S.; Greenberg, A.; Liebman, J. F. Eds; Chapman and Hall, London 1995; pp. 105-140.
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11. a) Elemes, Y.; Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1989, 30, 6903-06.
12. b) Orfanopoulos, M.; Stratakis, M.; Elemes, Y. Tetrahedron Lett. 1989, 30, 4875-78.
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18. Alkene 1 was prepared according to a literature procedure, starting from isobutyric acid and diethyl ketone : Adam, W.; Baeza, J.; Liu J-C. J. Am. Chem. Soc. 1972, 94, 2000-06. Alkenes 2-4 were prepared by mixed Ti(0) coupling of 4 equivalent of acetone with the 1 equivalent of the appropriate ketone : McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255-66.
19. Alkene 1 was prepared according to a literature procedure, starting from isobutyric acid and diethyl ketone : Adam, W.; Baeza, J.; Liu J-C. J. Am. Chem. Soc. 1972, 94, 2000-06. Alkenes 2-4 were prepared by mixed Ti(0) coupling of 4 equivalent of acetone with the 1 equivalent of the appropriate ketone : McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255-66.
20. Rautenstrauch, V.; Thommen, W.; Schulte-Elte, K. H. Helv. Chem. Acta 1986, 69, 1638-43.
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22. Seymour, C. A.; Greene F. D. J. Am. Chem. Soc. 1980, 102, 6384-85.