Juliá-Colonna oxidation reaction: Efficient access to chiral epoxides

Chimica Oggi

Volumn 21, Issue 9, 2003, Pages 6-8

  Geller, Thomas ^a   Gerlach, Arne ^b   Krüger, Christa M ^b   Militzer, H Christian ^b  

^a BAYER CROPSCIENCE AG   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE; LEUCINE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; EPOXIDATION; OXIDATION;

DRYAS IULIA;

EID: 2942624988     PISSN: 0392839X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. M. J. Porter, S. M. Roberts, J. Skidmore, Bioorg. Med Chem. 1999, 7, 2145-2156 and references cited therein
2. S. Juliá J. Masana, J. C. Vega, Angew. Chem., Int. Ed Engl. 1980, 19, 929
3. M. J. Porter, J. Skidmore, Chem Commun. 2000, 1215-1225 and references cited therein
4. a) J. R Flisak, P G George, I Lantos, W. L. Mendelson, 1990, EP 403252 A2;
5. b) K.-H. Drauz, S. M: Roberts, T. Geller, A. Dhanda, 2000, EP 1006127 A2;
6. c) K.-H. Drauz, S. M: Roberts, J. Skidmore, 2000, EP1006111 A2;
7. d) S M. Roberts, B. M. Adger, 1996, WO 9633183 A1
8. a) L. Carde, H. Davies, S M. Roberts, J Chem. Soc. Perkin Trans.1 2000, 2455-2463;
9. b) M. W. Cappi, W-P. Chen, R. W. Flood, Y.-W Liao, S. M Roberts, J. Skidmore, J. A Smith, N. M. Williamson. Chem. Commun. 1998, 1159-1160.
10. a) A. Dhanda, K.-H. Drauz, T. Geller, S. M. Roberts, Chirality 2000, 12, 313-317,
11. b) S. Banfi, S. Colonna, H. Molinari, S Juliá, J. Guixer. Tetrahedron 1984, 40, 5207-5211 and references cited therein:
12. c) P. A. Bentley, W. Kroutil, J. A. Littlechild, S. M. Roberts, Chirality 1997, 9, 198-202 and references cited therein
13. a) R. Takagi, A. Shiraki, T. Manabe, S. Kojima, K. Ohkata, Chem.Lett. 2000, 4, 366-367;
14. b) R. Takasi, T. Manabe, A. Shiraki, A. Yoneshige, Y. Hiraga, S Kojima, K. Ohkata. Bull Chem. Soc. Jpn. 2000, 73, 2115-2121;
15. c) R. W. Flood, T. P. Geller, S. A. Petty, S. M Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683-686;
16. d) P A. Bentley, R. W Flood, S. M Roberts, J. Skidmore, C. B Smith, J. A. Smith, Chem. Commun 2001, 1616-1617;
17. e) A Berkessel, N. Gasch, K Glaubitz, C. Koch, Org. Lett. 2001, 3, 3839-3842
18. PTCs have already been used for Juliá-Colonna reactions in order to utilise sparely water-soluble oxidants like Na-perborate or Na-percarbonate (4c,d,9). However, no beneficial additional effects on reaction time, selectivity and catalyst loading have been reported
19. M. E. Lasterra-Sánchez, U. Felfer, P Mayon, S. M. Roberts, S R. Thornton, C J. Todd, J. Chem Soc, Perkin Trans. I 1996, 343-348
20. S. M. Roberts, 1998, personal communication