Scale-up studies for the asymmetric Juliá-Colonna epoxidation reaction

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1247-1249

  Gerlach, Arne ^a   Geller, Thomas ^b  

^a BAYER AG   (Germany)

^b BAYER CROPSCIENCE AG   (Germany)

Author keywords

Amino acids; Asymmetric catalysis; Epoxidation; Heterogeneous catalysis; Phase transfer catalysis

Indexed keywords

KETONE DERIVATIVE; POLYAMINOACID;

CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; EPOXIDATION; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 5144225036     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404079     Document Type: Review

References (21)

1. a) S. Juliá, J. Masana, J. C. Vega, Angew. Chem. Int. Ed. Engl. 1980, 19, 929-931;
2. b) S. Juliá, J. Guixer, J. Masana, J. Rocas, S. Colonna, R. Annuziata, H. Molinari, J. Chem. Soc. Perkin Trans. 1 1982, 1317-1324.
3. a) C. Lauret, S. M. Roberts, Aldrichimica Acta 2002, 35, 47-51;
4. b) M. J. Porter, S. M. Roberts, J. Skidmore, Bioorg. Med. Chem. 1999, 7, 2145-2156.
5. [1] consists of an organic phase (toluene and starting material/product), an inorganic aqueous phase (sodium hydroxide and hydrogen peroxide) and a third solid phase (insoluble polyamino acid catalyst).
6. a) T. Geller, A. Gerlach, C. M. Krüger, H.-C. Militzer, Chimia Oggi/Chemistry Today 2003, 21, 6-8;
7. b) T. Geller, A. Gerlach, C. M. Krüger, H.-C. Militzer, Tetrahedron Lett. 2004, 45, 5065-5067.
8. E. P. Kohler, H. M. Chadwell, Org. Synth. Coll. Vol. I, 1941, 78-80.
9. Early screening experiments were conducted in magnetically stirred vials (5 mL) using 75 mg (0.24 mmol) of chalcone 2.
10. a) M. E. Lasterra-Sánchez, U. Felfer, P. Mayon, S. M. Roberts, S. R. Thornton, C. J. Todd, J. Chem. Soc. Perkin Trans. 1 1996, 343-348;
11. b) W. Kroutil, M. E. Lasterra-Sánchez, S. J. Maddrell, P. Mayon, P. Morgan, S. M. Roberts, S. R. Thornton, C. J. Todd, M. Tüter, J. Chem. Soc. Perkin Trans. 1 1996, 2837-2844;
12. c) P. A. Bentley, W. Kroutil, J. A. Littlechild, S. M. Roberts, Chirality 1997, 9, 198-202;
13. d) S. Baars, K.-H. Drauz, H.-P. Krimmer, S. M. Roberts, J. Sander, J. Skidmore, G. Zanardi, Org. Process Res. Dev. 2003, 7, 509-513.
14. a) F. Fuchs, Chem. Ber. 1922, 55, 2943;
15. b) A. C. Farthing, J. Chem. Soc. 1950, 3213-3217;
16. c) W. H. Daly, D. Poche, Tetrahedron Lett. 1988, 29, 5859-5862.
17. [7d]
18. Further washings or grinding of the crude poly-L-leucine 7 had no effect on enantioselectivity or reaction rate.
19. J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich, L. Snyder, J. Org. Chem. 1993, 58, 6247-6254.
20. This poly-L-leucine-1,3-diaminopropane catalyst is commercially available from Fluka (product number: 93197).
21. A single re-use of recovered poly-L-leucine catalyst 7 furnished epoxy ketone 4 in 75% yield with 97.3% ee after 20 hours on a 100 g substrate scale.