Studies of a diastereoselective electrophilic fluorination reaction employing a cryo-flow reactor

Synlett

Volumn 24, Issue 10, 2013, Pages 1298-1302

  Nakayama, Keiji ^a   Browne, Duncan L ^b   Baxendale, Ian R ^b   Ley, Steven V ^b  

^a Process Technology Research Laboratories   (Japan)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

chiral auxiliary; cryo flow reactor; diastereoselective fluorination; flow chemistry; polymer supported reagents

Indexed keywords

ELECTROPHILE;

BATCH PROCESS; CRYOFLOW REACTOR; DIASTEREOSELECTIVE FLUORINATION; FLOW KINETICS; FLUORINATION; LOW TEMPERATURE; REACTOR; REVIEW; STEREOCHEMISTRY;

EID: 84876389723     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1338455     Document Type: Review

References (37)

1. Now at Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.
2. Ma J.-A, Cahard D. Chem. Rev.: 2004; 104 6119
3. Hamashima Y., Sodeoka M. Synlett: 2006; 1467
4. Pihko P. M. Angew. Chem. Int. Ed.: 2006; 45 544
5. Shibata N., Ishimaru T., Nakamura S., Toru T. J. Fluorine Chem.: 2007; 128 469
6. Brunet V. A., O'Hagan D. Angew. Chem. Int. Ed.: 2008; 47 1179
7. Lectard S., Hamashima Y., Sodeoka M. Adv. Synth. Catal.: 2010; 352 2708
8. Nie J., Guo H.-C, Cahard D., Ma J.-A. Chem. Rev.: 2011; 111 455
9. Hennecke U. Angew. Chem. Int. Ed.: 2012; 51 4532
10. Brunet V. A., O'Hagan D., Slawin A. M. Z. J. Fluorine Chem.: 2007; 128 1271
11. Suzuki T., Hamashima Y., Sodeoka M. Angew. Chem. Int. Ed.: 2007; 5435
12. Peddie V., Butcher R. J., Robinson W. T., Wilce M. C. J, Traore D. A. K, Abell A. D. Chem. Eur. J.: 2012; 6655
13. Less S. L., Handa S., Millburn K., Leadlay P. F., Dutton C. J., Staunton J. Tetrahedron Lett.: 1996; 37 3515
14. Chen S.-H, Lamar J., Guo D., Kohn T., Yang H.-C, McGee J., Timm D., Erickson J., Yip Y., May P., McCarthy J. Bioorg. Med. Chem. Lett.: 2004; 14 245
15. Davis F. A., Han W. Tetrahedron Lett.: 1992; 33 1153
16. Edmonds M. K., Graichen F. H. M, Gardiner J., Abell A. D. Org. Lett.: 2008; 10 885
17. Peddie V., Pietsch M., Bromfield K. M., Pike R. N., Duggan P. J., Abell A. D. Synthesis: 2010; 1845
18. For a recent example with Fox auxiliary, see: Lubin H., Dupuis C., Pytkowicz J., Brigaud T. J. Org. Chem.: 2013; 78 3487
19. Polar Bear and Polar Bear Plus were purchased from Cambridge Reactor Design, CRD. http://www.cambridgereactordesign.com/index.html.
20. Browne D. L., Harji B. H., Ley S. V. Chem. Eng. Technol.: 2013; DOI: 10.1002/ceat.201200581
21. Browne D. L., Baumann M., Harji B. H., Baxendale I. R., Ley S. V. Org. Lett.: 2011; 13 3312
22. Shu W., Pellegatti L., Oberli M. A., Buchwald S. L. Angew. Chem. Int. Ed.: 2011; 50 10665
23. Sleveland D., Bjorsvik H.-R. Org. Process Res. Dev.: 2012; 16 1121
24. For a highlight of this topic, see: Desai A. A. Angew. Chem. Int. Ed.: 2012; 51 9223
25. Kralj J. G., Sahoo H. R., Jensen K. F. Lab Chip: 2007; 7 256
26. Atallah R. H., Ruzicka J., Christian G. D. Anal. Chem.: 1987; 59 2909
27. Castell O. K., Allender C. J., Barrow D. A. Lab Chip: 2009; 9 388
28. Kolehmainen E., Turunen I. Chem. Eng. Process.: 2007; 46 834
29. Hornung C. H., Mackley M. R., Baxendale I. R., Ley S. V. Org. Process Res. Dev.: 2007; 11 399
30. Sahoo H. R., Kralj J. G., Jensen K. F. Angew. Chem. Int. Ed.: 2007; 46 5704
31. O'Brien M., Koos P., Browne D. L., Ley S. V. Org. Biomol. Chem.: 2012; 10 7031
32. Hu D. X., O'Brien M., Ley S. V. Org. Lett.: 2012; 14 4246
33. Bourne S. L., O'Brien M., Kasinathan S., Koos P., Tolstoy P., Hu D. X., Bates R. W., Martin B., Schenkel B., Ley S. V. ChemCatChem: 2013; 5 159
34. Zhang Y., Kato S., Anazawa T. Lab Chip: 2010; 10 899
35. Hartman R. L., Sahoo H. R., Yen B. C., Jensen K. F. Lab Chip: 2009; 9 1843
36. Lam K. F., Cao E., Sorensen E., Gavriilidis A. Lab Chip: 2011; 11 1311
37. Browne D. L., Deadman B. J., Ashe R., Baxendale I. R., Ley S. V. Org. Process Res. Dev.: 2011; 15 693