A new cobalt-salen catalyst for asymmetric cyclopropanation. Synthesis of the serotonin-norepinephrine repuptake inhibitor (+)-synosutine

Organic Letters

Volumn 16, Issue 15, 2014, Pages 3880-3883

  White, James D ^a   Shaw, Subrata ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; COBALT; CYCLOPROPANE DERIVATIVE; NAPHTHALENE DERIVATIVE; NORADRENALIN; SEROTONIN UPTAKE INHIBITOR; SYNOSUTINE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; COBALT; CYCLOPROPANES; MOLECULAR STRUCTURE; NAPHTHALENES; NOREPINEPHRINE; SEROTONIN UPTAKE INHIBITORS; STEREOISOMERISM; THIOPHENES;

EID: 84905382420     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501549x     Document Type: Article

References (44)

1. Salaun, J. Chem. Rev. 1989, 89, 1247
2. Salaun, J. " Rearrangements Involving the Cyclopropyl Group ". In The Chemistry of the Cyclopropyl Group; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1987; Chapter 16.
3. Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977
4. Pellissier, H. Tetrahedron 2008, 64, 7041
5. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1965, 6, 2563
6. Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. 1992, 31, 430
7. Lesma, G.; Cattenati, C.; Pilati, T.; Sacchetti, A.; Silvani, A. Tetrahedron: Asymmetry 2007, 18, 659 and references cited therein
8. Bykowski, D.; Wu, K. H.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 16038
9. Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625
10. Shibata, Y.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 7896 and references cited therein
11. Berkessel, A.; Kaiser, P.; Lex, J. Chem.-Eur. J. 2003, 9, 4746
12. Charette, A. B.; Bouchard, J. E. Can. J. Chem. 2005, 83, 533
13. Miller, J. A.; Gross, B. A.; Zhuravel, M. A.; Jin, W. C.; Nguyen, S. T. Angew. Chem., Int. Ed. 2005, 44, 3885
14. Bonaccorsi, C.; Mezzetti, A. Organometallics 2005, 24, 4953 and references cited therein
15. Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647
16. Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79
17. Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521
18. Huang, L.; Chen, Y.; Gao, G.-Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 8179
19. Chen, Y.; Fields, K. B.; Zhang, X. P. J. Am. Chem. Soc. 2004, 126, 14718
20. Chen, Y.; Zhang, X. P. Synthesis 2006, 1697
21. Uchida, T.; Katsuki, T. Synthesis 2006, 1715
22. Chen, Y.; Zhang, X. P. J. Org. Chem. 2007, 72, 5931
23. Chen, Y.; Ruppel, J. V.; Zhang, X. P. J. Am. Chem. Soc. 2007, 129, 12074
24. Morandi, B.; Mariampillai, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 1101 and references cited therein
25. Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002
26. Watson, I. D. G.; Ritter, S.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 2056
27. Morandi, B.; Cheang, J.; Carreira, E. M. Org. Lett. 2011, 13, 3080
28. Morandi, B.; Dolva, A.; Carreira, E. M. Org. Lett. 2012, 14, 2162
29. Morandi, B.; Carreira, E. M. Science 2012, 335, 1471
30. Kaschel, J.; Schneider, T. F.; Weirz, D. B. Angew. Chem., Int. Ed. 2012, 51, 7085
31. Kanchiku, S.; Suematsu, H.; Matsumoto, K.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2007, 46, 3889
32. Ichinose, M.; Suematsu, H.; Katsuki, T. Angew. Chem., Int. Ed. 2009, 48, 3121
33. Anding, B. J.; Ellern, A.; Woo, L. K. Organometallics 2012, 31, 3628 and references cited therein
34. Zhang, J.; Liang, J. L.; Sun, X. R.; Zhou, H. B.; Zhu, N. Y.; Zhou, Z. Y.; Chan, P. W. H.; Che, C. M. Inorg. Chem. 2005, 44, 3942
35. White, J. D.; Shaw, S. Org. Lett. 2011, 13, 2488
36. White, J. D.; Shaw, S. Org. Lett. 2012, 14, 6270
37. White, J. D.; Shaw, S. Chem. Sci. 2014, 5, 2200
38. Theaker, G. W.; Morton, C.; Scott, P. Dalton Trans. 2008, 48, 6883
39. White, J. D.; Juniku, R.; Huang, K.; Yang, J.; Wong, D. T. J. Med. Chem. 2009, 52, 5872
40. Charette, A. B.; Juteau, H. J. Am. Che. Soc. 1994, 116, 2651
41. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611
42. The " trans effect " associated with sulfur-metal coordination which enhances reactivity at the metal center is documented. For a review, see: Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5
43. Klein, H. F.; Beck, R.; Florke, U.; Haupt, H. J. Eur. J. Inorg. Chem. 2002, 3305
44. Klein, H. F.; Beck, R.; Florke, U.; Haupt, H. J. Eur. J. Inorg. Chem. 2003, 1380