Asymmetric synthesis of 1,3-aminoketals

Tetrahedron Asymmetry

Volumn 16, Issue 22, 2005, Pages 3650-3660

  Bariau, Annabelle ^a   Canet, Jean Louis ^a   Chalard, Pierre ^a   Troin, Yves ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AMIDE; ESTER DERIVATIVE; LITHIUM DERIVATIVE; PIPERIDINE;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY;

EID: 27944493998     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.09.024     Document Type: Article

References (65)

1. S. Rougnon-Glasson, J.-L. Canet, and Y. Troin Tetrahedron Lett. 41 2000 9797 9798
2. S. Ciblat, P. Besse, J.-L. Canet, Y. Troin, H. Veschambre, and J. Gelas Tetrahedron: Asymmetry 10 1999 2225 2235
3. S. Carbonnel, C. Fayet, J. Gelas, and Y. Troin Tetrahedron Lett. 41 2000 8293 8296
4. E. Wenkert, K.G. Dave, and R.-V. Stevens J. Am. Chem. Soc. 90 1968 6177 6182
5. J. Bosch, M. Rubiralta, and M. Moral Heterocycles 19 1982 473 476
6. S. Ciblat, P. Besse, V. Papastergiou, H. Veschambre, J.-L. Canet, and Y. Troin Tetrahedron: Asymmetry 11 2000 2221 2229
7. S. Ciblat, P. Calinaud, J.-L. Canet, and Y. Troin J. Chem. Soc., Perkin Trans. 1 2000 353 357
8. S. Rougnon-Glasson, C. Tratrat, J.-L. Canet, P. Chalard, and Y. Troin Tetrahedron: Asymmetry 15 2004 1561 1567
9. S. Carbonnel, and Y. Troin Heterocycles 57 2002 1807 1830
10. A. Bariau, J.-P. Roblin, Y. Troin, and J.-L. Canet Synlett 11 2005 1731 1733
11. J. Barluenga, B. Olano, S. Fustero, M. Foces, and F.H. Cano J. Chem. Soc., Chem. Commun. 1988 410 412
12. J.E. Baldwin, R.M. Adlington, A.T. Russell, and M.L. Smith Tetrahedron 51 1995 4733 4762
13. C. Palomo, J.M. Aizpurua, J.M. Garcia, M. Iturburu, and J.M. Odriozola J. Org. Chem. 59 1994 5184 5188
14. D.M. Spero, S. Kapadia, and V. Farina Tetrahedron Lett. 36 1995 4543 4546
15. I. Ojima, E.W. Ng, and C.M. Sun Tetrahedron Lett. 36 1995 4547 4550
16. H.K. Lee, E.K. Kim, and S. Pak Tetrahedron Lett. 43 2002 9641 9644
17. S.G. Davies, and T.D. McCarthy Synlett 1995 700 702
18. F.A. Davis, and B. Yang Org. Lett. 5 2003 5011 5014
19. F.A. Davis, M.B. Nolt, Y. Wu, K.R. Prasad, D. Li, B. Yang, K. Bowen, S.H. Lee, and J.H. Eardley J. Org. Chem. 70 2005 2184 2190
20. A.J. Burke, S.G. Davies, A.C. Garner, T.D. McCarthy, P.M. Roberts, A.D. Smith, H. Rodriguez-Sola, and R.J. Vickers Org. Biomol. Chem. 2 2004 1387 1394
21. F.A. Davis, and B. Yang J. Am. Chem. Soc. 127 2005 8398 8407
22. F.A. Davis, J. Zhang, Y. Li, H. Xu, and C. De Brosse J. Org. Chem. 70 2005 5413 5419
23. M. Arend, B. Westermann, and N. Risch Angew. Chem., Int. Ed. Engl. 37 1998 1044 1070
24. A. Zarghi, M.R. Naimi Jamal, S.A. Webb, S. Balalaie, M.R. Saidi, and J. Ipaktshi Eur. J. Org. Chem. 1998 197 200
25. K. Ishimaru, and T. Kojima Tetrahedron Lett. 42 2001 5037 5039
26. F.A. Davis, K.R. Prasad, M.B. Nolt, and Y. Wu Org. Lett. 4 2002 925 927
27. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069 1094
28. A. Cordova Acc. Chem. Res. 37 2004 102 112
29. S. Kobayashi, R. Matsubara, and H. Kitagawa Org. Lett. 4 2002 143 145
30. B.M. Trost, and L.R. Terrell J. Am. Chem. Soc. 125 2003 338 339
31. S. Matsunaga, N. Kamagai, S. Harada, and M. Shibasaki J. Am. Chem. Soc. 125 2003 4712 4713
32. B. List J. Am. Chem. Soc. 122 2000 9336 9337
33. B. List, P. Pojarliev, W.T. Biller, and H.J. Martin J. Am. Chem. Soc. 124 2002 827 833
34. W. Notz, K. Sakthivel, T. Bui, G. Zhong, and C.F. Barbas III Tetrahedron Lett. 42 2001 199 201
35. M.P. Sibi Organic Preparations and Procedures Int 25 1993 15 40
36. J. Singh, N. Satyamurthi, and I.S. Aidhen J. Prakt. Chem. 342 2000 340 347
37. S.G. Davies, and O. Ichihara Tetrahedron: Asymmetry 2 1991 183 186
38. J.F. Costello, S.G. Davies, and O. Ichihara Tetrahedron: Asymmetry 5 1994 1999 2008
39. S.G. Davies, and I.A.S. Walters J. Chem. Soc., Perkin Trans. 1 1994 1129 1139
40. S.G. Davies, O. Ichihara, and I.A.S. Walters J. Chem. Soc., Perkin Trans. 1 1994 1141 1147
41. S.D. Bull, S.G. Davies, P.M. Kelly, M. Gianotti, and A.D. Smith J. Chem. Soc., Perkin Trans. 1 2001 3106 3111
42. S.L. Graham, and T. Scholtz Tetrahedron Lett. 31 1990 6269 6272
43. M.P. Sibi, M. Marvin, and R. Sharma J. Org. Chem. 60 1995 5016 5023
44. J.C. Anderson, A. Flaherty, and M.E. Swarbrick J. Org. Chem. 65 2000 9152 9156
45. V. Selvamurugan, and I.S. Aidhen Tetrahedron 57 2001 6065 6070
46. O. Labeeuw, D. Blanc, P. Phansavath, V. Ratovelomanana-Vidal, and J.P. Genet Eur. J. Org. Chem. 2004 2352 2358
47. R.M. Adlington, J.E. Baldwin, D. Catterick, and G.J. Pritchard J. Chem. Soc., Perkin Trans. 1 1999 855 866
48. M.T. Reetz, M.W. Drewes, K. Lennick, A. Schmitz, and X. Holdgrün Tetrahedron: Asymmetry 1 1990 375 378
49. D. Lucet, T. Le Gall, C. Mioskowski, O. Ploun, and A. Marquet Tetrahedron: Asymmetry 7 1996 985 988
50. D.L. Rieger J. Org. Chem. 62 1997 8546 8548
51. F. Osawa, M. Nakano, I. Aoyama, T. Yamamoto, and A. Yamamoto J. Chem. Soc., Chem. Commun. 5 1986 382 383
52. S. Manfredi, D. Simoni, V. Zanirato, and A. Casolari Tetrahedron Lett. 29 1988 3997 4000
53. A. Barco, S. Benetti, and G.P. Pollini J. Org. Chem. 46 1981 4518 4524
54. T. Tsunoda, M. Suzuki, and R. Noyori Tetrahedron Lett. 21 1980 1357 1358
55. H. Esterman, and D. Seebach Helvetica Chim. Acta 71 1988 1824 1839
56. M.J. Munchhof, and A.I. Meyers J. Am. Chem. Soc. 117 1995 5399 5400
57. Loupy, A.; Tchoubar, B. In Effets de sels en chimie organique et organométallique; Dunod Paris, Dunod Université, 1988.
58. M.P. Periasamy, and H.M. Walborsky J. Am. Chem. Soc. 99 1977 2631 2638
59. P.R. Jenkins Organometallic Reagents in Synthesis 1992 Oxford Sciences Publications-Oxford University Press
60. M.A.T. Maughan, I.G. Davies, T.D.W. Claridge, S. Courtney, P. Hay, and B.G. Davis Angew. Chem., Int. Ed. 42 2003 3788 3792
61. O. Peters, T. Debaerdemaeker, and W. Friedrichsen J. Chem. Soc., Perkin Trans. 1 1999 59 70
62. F. Gosselin, and W.D. Lubell J. Org. Chem. 63 1998 7441 7463
63. G. Solladie, N. Gehrold, and J. Maignan Eur. J. Org. Chem. 1999 2309 2314
64. D. Ma, and H. Sun J. Org. Chem. 65 2000 6009 6016
65. P. Chalard, R. Remuson, Y. Gelas-Mialhe, and J.-C. Gramain Tetrahedron: Asymmetry 9 1998 4361 4368