Stereoselective synthesis of configurationally stable functionalized ethano-bridged Tröger bases

Chemical Communications

Volumn 46, Issue 13, 2010, Pages 2206-2208

  Michon, Christophe ^a   Sharma, Ankit ^a   Bernardinelli, Gérard ^b   Francotte, Eric ^c   Lacour, Jérôme ^a  

^a Department of Organic Chemistry ^*  (Switzerland)

^b UNIVERSITY OF GENEVA   (Switzerland)

^c NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; BRIDGED COMPOUND;

ALKYLATION; ARTICLE; MOLECULAR STABILITY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 77949579817     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b925065d     Document Type: Article

References (56)

1. J. Tröger J. Prakt. Chem. 1887 36 225 245
2. S. Sergeyev Helv. Chim. Acta 2009 92 415 444
3. B. Dolensky J. Elguero V. Kral C. Pardo M. Valik Adv. Heterocycl. Chem. 2007 93 1 56
4. M. Demeunynck A. Tatibouet Prog. Heterocycl. Chem. 1999 11 1 20
5. C. Pardo I. Alkorta J. Elguero Tetrahedron: Asymmetry 2006 17 191 198
6. V. Galasso D. Jones A. Modelli Chem. Phys. 2003 288 33 42
7. A. Aamouche F. J. Devlin P. J. Stephens J. Am. Chem. Soc. 2000 122 2346 2354
8. S. H. Wilen J. Z. Qi P. G. Williard J. Org. Chem. 1991 56 485 487
9. T. R. Miller E. C. Wagner J. Am. Chem. Soc. 1941 63 832 836
10. M. A. Spielman J. Am. Chem. Soc. 1935 57 583 585
11. H. Wu X. M. Chen Y. Wan L. Ye H. Q. Xin H. H. Xu C. H. Yue L. L. Pang R. Ma D. Q. Shi Tetrahedron Lett. 2009 50 1062 1065
12. E. Vardelle A. Martin-Mingot M. P. Jouannetaud J. C. Jacquesy J. Marrot Tetrahedron Lett. 2009 50 1093 1096
13. A. B. Mahon D. C. Craig A. C. Try Synthesis 2009 636 642
14. M. Faroughi K. X. Zhu P. Jensen D. C. Craig A. C. Try Eur. J. Org. Chem. 2009 4266 4272
15. J. Artacho K. Warnmark Synthesis 2009 3120 3126
16. M. Havlik V. Kral R. Kaplanek B. Dolensky Org. Lett. 2008 10 4767 4769
17. M. Faroughi A. C. Try J. Klepetko P. Turner Tetrahedron Lett. 2007 48 6548 6551
18. D. Didier S. Sergeyev Eur. J. Org. Chem. 2007 3905 3910
19. S. Satishkumar M. Periasamy Tetrahedron: Asymmetry 2006 17 1116 1119
20. Y. Ishida H. Ito D. Mori K. Saigo Tetrahedron Lett. 2005 46 109 112
21. S. Sergeyev F. Diederich Angew. Chem., Int. Ed. 2004 43 1738 1740
22. Y. Miyahara K. Izumi A. A. Ibrahim T. Inazu Tetrahedron Lett. 1999 40 1705 1708
23. M. Harmata M. Kahraman Tetrahedron: Asymmetry 2000 11 2875 2879
24. S. Satishkumar M. Periasamy Tetrahedron: Asymmetry 2009 20 2257 2262
25. M. Valik J. Cejka M. Havlik V. Kral B. Dolensky Chem. Commun. 2007 3835 3837
26. E.-I. Kim S. Paliwal C. S. Wilcox J. Am. Chem. Soc. 1998 120 11192 11193
27. M. J. Crossley L. G. Mackay A. C. Try J. Chem. Soc., Chem. Commun. 1995 1925 1927
28. E. Weber U. Müller D. Worsch F. Vögtle G. Will A. Kirfel J. Chem. Soc., Chem. Commun. 1985 1578 1580
29. E. B. Veale D. O. Frimannsson M. Lawler T. Gunnlaugsson Org. Lett. 2009 11 4040 4043
30. A. Tatibouët M. Demeunynck C. Andraud A. Collet J. Lhomme Chem. Commun. 1999 161 162
31. C. S. Wilcox M. D. Cowart Tetrahedron Lett. 1986 27 5563 5566
32. T. Weilandt U. Kiehne G. Schnakenburg A. Lutzen Chem. Commun. 2009 2320 2322
33. Y. M. Jeon G. S. Armatas D. Kim M. G. Kanatzidis C. A. Mirkin Small 2009 5 46 50
34. M. S. Khoshbin M. V. Ovchinnikov C. A. Mirkin J. A. Golen A. L. Rheingold Inorg. Chem. 2006 45 2603 2609
35. U. Kiehne T. Bruhn G. Schnakenburg R. Frohlich G. Bringmann A. Lützen Chem.-Eur. J. 2008 14 4246 4255
36. V. Prelog P. Wieland Helv. Chim. Acta 1944 27 1127 1134
37. D. A. Lenev K. A. Lyssenko D. G. Golovanov V. Buss R. G. Kostyanovsky Chem.-Eur. J. 2006 12 6412 6418
38. O. Trapp G. Trapp J. W. Kong U. Hahn F. Vögtle V. Schurig Chem.-Eur. J. 2002 8 3629 3634
39. D. A. Lenev D. G. Golovanov K. A. Lyssenko R. G. Kostyanovsky Tetrahedron: Asymmetry 2006 17 2191 2194
40. Y. Hamada S. Mukai Tetrahedron: Asymmetry 1996 7 2671 2674
41. C. Michon M. H. Goncalves-Farbos J. Lacour Chirality 2009 21 809 817
42. L. Vial J. Lacour Org. Lett. 2002 4 3939 3942
43. J. Lacour L. Vial C. Herse Org. Lett. 2002 4 1351 1354
44. J. A. Vanecko H. Wan F. G. West Tetrahedron 2006 62 1043 1062
45. I. E. Markó, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming, Pergamon Press, Oxford, 1991, pp. 913-974
46. M.-H. Gonalves-Farbos L. Vial J. Lacour Chem. Commun. 2008 829 831
47. L. Vial M.-H. Gonalves P.-Y. Morgantini J. Weber G. Bernardinelli J. Lacour Synlett 2004 1565 1568
48. M. Häring Helv. Chim. Acta 1963 46 2970 2982
49. F. C. Cooper M. W. Partridge J. Chem. Soc. 1957 2888 2893
50. A variety of organic and inorganic bases were used. For details, please consult the reagents used in conjunction with salt [3b][Br]
51. X. M. Zhang F. G. Bordwell J. Am. Chem. Soc. 1994 116 968 972
52. all = 1.05(2)
53. X. H. Bu M. Du L. J. Zhao K. Tanaka M. Shionoya M. Shiro J. Chem. Res. (S) 2001 2001 243 245
54. G. J. Cox, Preparative Enantioselective Chromatography, Blackwell Pub., Ames, Iowa, 2005
55. E. R. Francotte J. Chromatogr. A 2001 906 379 397
56. -1. UV 210 nm. The electronic circular dichroism (ECD) spectra of the separated enantiomers are reported in the ESI The reason for this surprising loss is still under evaluation