Cyclopropanation using flow-generated diazo compounds

Organic and Biomolecular Chemistry

Volumn 13, Issue 9, 2015, Pages 2550-2554

  Roda, Nuria M ^a   Tran, Duc N ^a   Battilocchio, Claudio ^a   Labes, Ricardo ^a   Ingham, Richard J ^a   Hawkins, Joel M ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3D BUILDINGS; CONTINUOUS FLOWS; CYCLOPROPANATION; DIAZO COMPOUNDS; ROOM-TEMPERATURE PROCESS;

POSITIVE IONS;

AZO COMPOUND; CYCLOPROPANE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZO COMPOUNDS; CYCLOPROPANES; MOLECULAR STRUCTURE;

EID: 84931955063     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob00019j     Document Type: Article

References (43)

1. R. L. Hartman J. P. McMullen K. F. Jensen Angew. Chem., Int. Ed. 2011 50 7502 7519
2. J. Wegner S. Ceylan A. Kirschning Adv. Synth. Catal. 2012 354 17 57
3. C. Wiles P. Watts Green Chem. 2012 14 38 54
4. L. Malet-Sanz F. Susanne J. Med. Chem. 2012 55 4062 4098
5. I. R. Baxendale J. Chem. Technol. Biotechnol. 2013 88 519 552
6. J. C. Pastre D. L. Browne S. V. Ley Chem. Soc. Rev. 2013 42 8849 8869
7. S. V. Ley D. E. Fitzpatrick R. J. Ingham R. M. Myers Angew. Chem., Int. Ed. 2014 53 2 17
8. H. Kim A. Nagaki J.-I. Yoshida Nat. Commun. 2011 2 264
9. F. Levesque P. H. Seeberger Angew. Chem., Int. Ed. 2012 51 1706 1709
10. B. J. Deadman C. Battilocchio E. Sliwinski S. V. Ley Green Chem. 2013 15 2050 2055
11. Z. He T. F. Jamison Angew. Chem., Int. Ed. 2014 53 3353 3357
12. M. Baumann I. R. Baxendale Beilstein J. Org. Chem. 2013 9 1613 1619
13. S. Newton C. F. Carter C. M. Pearson L. de C. Alves H. Lange P. Thansandote S. V. Ley Angew. Chem., Int. Ed. 2014 53 4915 4920
14. A. M. Nightingale T. W. Phillips J. H. Bannock J. C. de Mello Nat. Commun. 2014 5 3777
15. X. Fan V. Sans P. Yaseneva D. D. Plaza J. Williams A. Lapkin Org. Process Res. Dev. 2012 16 1039 1042
16. S. Glöckner D. N. Tran R. J. Ingham S. Fenner Z. E. Wilson C. Battilocchio S. V. Ley Org. Biomol. Chem. 2015 13 207 214
17. T. Ouchi C. Battilocchio J. M. Hawkins S. V. Ley Org. Process Res. Dev. 2014 18 1560 1566
18. F. Mastronardi B. Gutmann C. O. Kappe Org. Lett. 2013 15 5590 5593
19. D. N. Tran C. Battilocchio S.-B. Lou J. M. Hawkins S. V. Ley Chem. Sci. 10.1039/C4SC03072A
20. B. J. Deadman S. G. Collins A. R. Maguire Chem.-Eur. J. 10.1002/chem.201404348
21. W. A. Donaldson Tetrahedron 2001 57 8589 8627
22. H. Lebel J.-F. Marcoux C. Molinaro A. B. Charette Chem. Rev. 2003 103 977 1050
23. L. A. Wessjohann W. Brandt T. Thiemann Chem. Rev. 2003 103 1625 1648
24. F. Brackmann A. de Meijere Chem. Rev. 2007 107 4493 4537
25. J.-J. Shen S.-F. Zhu Y. Cai H. Xu X.-L. Xie Q.-L. Zhou Angew. Chem., Int. Ed. 2014 53 13188 13191
26. V. N. G. Lindsay D. Fiset P. J. Gritsch S. Azzi A. B. Charette J. Am. Chem. Soc. 2013 135 1463 1470
27. X. Xu H. J. Lu J. V. Ruppel X. Cui S. L. de Mesa L. Wojtas X. P. Zhang J. Am. Chem. Soc. 2011 133 15292 15295
28. S. F. Zhu X. Xu J. A. Perman X. P. Zhang J. Am. Chem. Soc. 2010 132 12796 12799
29. M. P. Doyle Angew. Chem., Int. Ed. 2009 48 850 852
30. M. Doyle Acc. Chem. Res. 1986 19 348 356
31. A. J. Padwa Organomet. Chem. 2001 617 3 16
32. M. Regitz and G. Mass, Diazo Compounds Properties and Synthesis, Academic Press, Inc., Orlando, 1986
33. M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998
34. J. N. Johnston H. Muchalski T. L. Troyer Angew. Chem., Int. Ed. 2010 49 2290 2298
35. G. Maas Angew. Chem., Int. Ed. 2009 48 8186 8195
36. V. L. Rendina J. S. Kingsbury J. Org. Chem. 2012 77 1181 1185
37. A. J. Wommack J. S. Kingsbury J. Org. Chem. 2013 78 10573 10587
38. T. L. Holton H. Shechter J. Org. Chem. 1995 60 4725 4729
39. L. A. Adams V. K. Aggarwal R. V. Bonnert B. Bressel R. J. Cox J. Shepherd J. de Vicente M. Walter W. G. Whittingham C. L. Winn J. Org. Chem. 2003 68 9433 9440
40. T. F. Schneider J. Kaschel D. B. Werz Angew. Chem., Int. Ed. 2014 53 5504 5523
41. M. A. Cavitt L. H. Phun S. France Chem. Soc. Rev. 2014 43 804 818
42. I. Hemeon N. W. Barnett N. Gathergood P. J. Scammells R. D. Singer Aust. J. Chem. 2004 57 125 128
43. I. Bhatnagar M. V. George J. Org. Chem. 1968 33 2407 2411