Rapid access to α-alkoxy and α-amino acid derivatives through safe continuous-flow generation of diazoesters

Chemistry - A European Journal

Volumn 17, Issue 35, 2011, Pages 9586-9589

  Bartrum, Hannah E ^a   Blakemore, David C ^b   Moody, Christopher J ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

amino acids; carbenoids; continuous flow chemistry; diazo compounds

Indexed keywords

AMINO ACID DERIVATIVES; CARBENOIDS; CONTINUOUS-FLOW; CONTINUOUS-FLOW PROCESS; DIAZO COMPOUNDS; MICRO REACTOR; N-H INSERTION;

CHEMICAL REACTORS; RHODIUM; RHODIUM COMPOUNDS;

AMINO ACIDS;

ALKANE; AMINO ACID; AZO COMPOUND; AZOESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKANES; AMINO ACIDS; AZO COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80051735851     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101590     Document Type: Article

References (30)

1. T. Ye, A. McKervey, Chem. Rev. 1994, 94, 1091-1160
2. A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-269
3. M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911-935
4. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2903
5. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998.
6. Ethyl and butyl diazoacetate, TMS-diazomethane and diazodimedone are all available from Sigma Aldrich.
7. G. Maas, Angew. Chem. 2009, 121, 8332-8341
8. Angew. Chem. Int. Ed. 2009, 48, 8186-8195.
9. R. C. Wheeler, O. Benali, M. Deal, E. Farrant, S. J. F. MacDonald, B. H. Warrington, Org. Process Res. Dev. 2007, 11, 704-710.
10. L. J. Martin, A. L. Marzinzik, S. V. Ley, I. R. Baxendale, Org. Lett. 2011, 13, 320-323
11. I. R. Baxendale, S. V. Ley, A. C. Mansfield, C. D. Smith, Angew. Chem. 2009, 121, 4077-4081
12. Angew. Chem. Int. Ed. 2009, 48, 4017-4021.
13. P. B. Palde, T. F. Jamison, Angew. Chem. 2011, 123, 3587-3590
14. Angew. Chem. Int. Ed. 2011, 50, 3525-3528.
15. B. Gutmann, J-P. Roduit, D. Roberge, C. O. Kappe, Angew. Chem. 2010, 122, 7255-7259
16. Angew. Chem. Int. Ed. 2010, 49, 7101-7105.
17. L. D. Proctor, A. J. Warr, Org. Process Res. Dev. 2002, 6, 884-892.
18. J. D. Clark, J. D. Heise, A. S. Shah, J. C. Peterson, S. K. Chou, J. Levine, A. M. Karakas, Y. Ma, K-Y. Ng, L. Patelis, J. R. Springer, D. R. Stano, R. H. Wettach, G. A. Dutra, Org. Process Res. Dev. 2004, 8, 176-185.
19. P. Pollet, E. D. Cope, M. K. Kassner, R. Charney, S. H. Terett, K. W. Richman, W. Dubay, J. Stringer, C. A. Eckert, C. L. Liotta, Ind. Eng. Chem. Res. 2009, 48, 7032-7036.
20. H. E. Bartrum, D. C. Blakemore, C. J. Moody, C. J. Hayes, J. Org. Chem. 2010, 75, 8674-8676.
21. W. R. Bamford, T. S. Stevens, J. Chem. Soc. 1952, 4735-4740.
22. M. Regitz, G. Maas, Diazocompounds: Properties and Synthesis, Academic Press, New York, 1986.
23. J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem. 2005, 1479-1492.
24. For previous thermal stability studies on ethyl diazoacetate see:, J. D. Clark, A. S. Shah, J. C. Peterson, L. Patelis, R. J. A. Kersten, A. H. Heemskerk, M. Grogan, S. Camden, Thermochimica Acta 2002, 386, 65-72.
25. D. J. Miller, C. J. Moody, C. N. Morfitt, Aust. J. Chem. 1999, 52, 97-107.
26. G. Shi, Y. Xu, J. Chem. Soc. Chem. Commun. 1989, 607-608.
27. C. C. Dudman, C. B. Reese, Synthesis 1982, 419-421.
28. PFA=perfluoroalkoxy polymer.
29. D. J. Miller, C. J. Moody, Tetrahedron 1995, 51, 10811-10843.
30. E. Aller, R. T. Buck, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson, J. B. Sanghera, J. Chem. Soc. Perkin Trans. 1 1996, 2879-2884.