Sterically encumbered chiral amino alcohols for titanium-catalyzed asymmetric intramolecular hydroamination of aminoallenes

Tetrahedron Asymmetry

Volumn 20, Issue 11, 2009, Pages 1279-1285

  Hickman, Amanda J ^a   Hughs, Lauren D ^a   Jones, Casey M ^a   Li, Hanhan ^a   Redford, Joanne E ^a   Sobelman, Samuel J ^a   Kouzelos, J Andrew ^a   Johnson, Adam R ^a  

^a HARVEY MUDD COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; AMINE; AMINOALCOHOL; PYRROLIDINE DERIVATIVE; TITANIUM;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 67649397420     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.04.013     Document Type: Article

References (83)

1. Hultzsch K.C. Adv. Synth. Catal. 347 (2005) 367-391
2. Hultzsch K.C. Org. Biomol. Chem. 3 (2005) 1819-1824
3. Pohlki F., and Doye S. Chem. Soc. Rev. 32 (2003) 104-114
4. Müller T.E., and Beller M. Chem. Rev. 98 (1998) 675-703
5. Doye S. Synlett (2004) 1653-1672
6. Hong S., and Marks T.J. Acc. Chem. Res. 37 (2004) 673-686
7. Müller T.E., Hultzsch K.C., Yus M., Foubelo F., and Tada M. Chem. Rev. 108 (2008) 3795-3892
8. Seayad J., Tillack A., Hartung C.G., and Beller M. Adv. Synth. Catal. 344 (2002) 795-813
9. Quinet C., Jourdain P., Hermans C., Ates A., Lucas I., and Markó I.E. Tetrahedron 64 (2008) 1077-1087
10. Horrillo-Martinez P., Hultzsch K.C., Gil A., and Branchadell V. Eur. J. Org. Chem. (2007) 3311-3325
11. Zhang W., Werness J.B., and Tang W.P. Org. Lett. 10 (2008) 2023-2026
12. Odom A.L. Dalton Trans. (2005) 225-233
13. Lee A.V., and Schafer L.L. Eur. J. Inorg. Chem. (2007) 2243-2255
14. Bytschkov I., and Doye S. Eur. J. Org. Chem. (2003) 935-946
15. Ackermann L., Kaspar L.T., and Althammer A. Org. Biomol. Chem. 5 (2007) 1975-1978
16. Kim H., Livinghouse T., and Lee P.H. Tetrahedron 64 (2008) 2525-2529
17. Hii K.K. Pure Appl. Chem. 78 (2006) 341-349
18. Bender C.F., Hudson W.B., and Widenhoefer R.A. Organometallics 27 (2008) 2356-2358
19. Nishina N., and Yamamoto Y. Synlett (2007) 1767-1770
20. Nishina N., and Yamamoto Y. Angew. Chem., Int. Ed. 45 (2006) 3314-3317
21. Bender C.F., and Widenhoefer R.A. Chem. Commun. (2008) 2741-2743
22. Ritter S., Hackeloer K., and Schmalz H.G. Heterocycles 74 (2007) 731-742
23. Li Z., Brouwer C., and He C. Chem. Rev. 108 (2008) 3239-3265
24. Arcadi A. Chem. Rev. 108 (2008) 3266-3325
25. Lavallo V., Frey G.D., Donnadieu B., Soleilhavoup M., and Bertrand G. Angew. Chem., Int. Ed. 47 (2008) 5224-5228
26. Hultzsch K.C., Gribkov D.V., and Hampel F. J. Org. Chem. 690 (2005) 4441-4452
27. Datta S., Gamer M.T., and Roesky P.W. Organometallics 27 (2008) 1207-1213
28. Kim H., Livinghouse T., Shim J.H., Lee S.G., and Lee P.H. Adv. Synth. Catal. 348 (2006) 701-704
29. Kim H., Livinghouse T., Seomoon D., and Lee P.H. Bull. Korean Chem. Soc. 28 (2007) 1127-1134
30. Bexrud J.A., Beard J.D., Leitch D.C., and Schafer L.L. Org. Lett. 7 (2005) 1959-1962
31. Thomson R.K., Bexrud J.A., and Schafer L.L. Organometallics 25 (2006) 4069-4071
32. Majumder S., and Odom A.L. Organometallics 27 (2008) 1174-1177
33. Muller C., Loos C., Schulenberg N., and Doye S. Eur. J. Org. Chem. (2006) 2499-2503
34. Muller C., Saak W.G., and Doye S. Eur. J. Org. Chem. (2008) 2731-2739
35. Gribkov D.V., and Hultzsch K.C. Angew. Chem., Int. Ed. 43 (2004) 5542-5546
36. Beesley R.M., Ingold C.K., and Thorpe J.F. J. Chem. Soc. (1915) 1080-1106
37. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735-1766
38. Johnson J.S., and Bergman R.G. J. Am. Chem. Soc. 123 (2001) 2923-2924
39. Arredondo V., McDonald F.E., and Marks T.J. Organometallics 18 (1999) 1949-1960
40. Ayinla R.O., and Schafer L.L. Inorg. Chim. Acta 359 (2006) 3097-3102
41. Arseniyadis S., and Gore J. Tetrahedron Lett. 24 (1983) 3997-4000
42. Kinsman R., Lathbury D., Vernon P., and Gallagher T. J. Chem. Soc., Chem. Commun. (1987) 243-244
43. Fox D.N.A., and Gallagher T. Tetrahedron 46 (1990) 4697-4710
44. Meguro M., and Yamamoto Y. Tetrahedron Lett. 39 (1998) 5421-5424
45. Ackermann L., and Bergman R.G. Org. Lett. 4 (2002) 1475-1478
46. Ackermann L., Bergman R.G., and Loy R.N. J. Am. Chem. Soc. 125 (2003) 11956-11963
47. Arredondo V., McDonald F.E., and Marks T.J. J. Am. Chem. Soc. 120 (1998) 4871-4872
48. Arredondo V., Tian S., McDonald F.E., and Marks T.J. J. Am. Chem. Soc. 121 (1999) 3633-3639
49. Tobisch S. Chem. Eur. J. 13 (2007) 4884-4894
50. Tobisch S. Dalton Trans. (2006) 4277-4285
51. Gagne M.R., Brard L., Conticello V.P., Giardello M.A., Stern C.L., and Marks T.J. Organometallics 11 (1992) 2003-2005
52. Giardello M.A., Conticello V.P., Brard L., Gagne M.R., and Marks T.J. J. Am. Chem. Soc. 116 (1994) 10241-10254
53. Douglass M.R., Ogasawara M., Hong S., Metz M.V., and Marks T.J. Organometallics 21 (2002) 283-292
54. Ryu J.-S., Marks T.J., and McDonald F.E. J. Org. Chem. 69 (2004) 1038-1052
55. Aillaud I., Collin J., Hannedouche J., and Schulz E. Dalton Trans. (2007) 5105-5118
56. Roesky P.W., and Müller T.E. Angew. Chem., Int. Ed. 42 (2003) 2708-2710
57. Collin J., Daran J.C., Jacquet O., Schulz E., and Trifonov A. Chem. Eur. J. 11 (2005) 3455-3462
58. Gribkov D.V., Hultzsch K.C., and Hampel F. J. Am. Chem. Soc. 128 (2006) 3748-3759
59. Riegert D., Collin J., Meddour A., Schulz E., and Trifonov A. J. Org. Chem. 71 (2006) 2514-2517
60. Yu X.H., and Marks T.J. Organometallics 26 (2007) 365-376
61. Wang Q.W., Xiang L., Song H.B., and Zi G.F. Inorg. Chem. 47 (2008) 4319-4328
62. Zi G.G., Xiang L., and Song H.B. Organometallics 27 (2008) 1242-1246
63. Gott A.L., Clarke A.J., Clarkson G.J., and Scott P. Organometallics 26 (2007) 1729-1737
64. Wood M.C., Leitch D.C., Yeung C.S., Kozak J.A., and Schafer L.L. Angew. Chem., Int. Ed. 46 (2007) 354-358
65. Gribkov D.V., and Hultzsch K.C. Chem. Commun. (2004) 730-731
66. Kim H., Kim Y.K., Shim J.H., Kim M., Han M.J., Livinghouse T., and Lee P.H. Adv. Synth. Catal. 348 (2006) 2609-2618
67. Kim J.Y., and Livinghouse T. Org. Lett. 7 (2005) 1737-1739
68. Knight P.D., Munslow I., O'Shaughnessy P.N., and Scott P. Chem. Commun. (2004) 894-895
69. O'Shaughnessy P.N., Gillespie K.M., Knight P.D., Munslow I.J., and Scott P. Dalton Trans. (2004) 2251-2256
70. Riegert D., Collin J., Daran J.C., Fillebeen T., Schulz E., Lyubov D., Fukin G., and Trifonov A. Eur. J. Inorg. Chem. (2007) 1159-1168
71. Watson D.A., Chiu M., and Bergman R.G. Organometallics 25 (2006) 4731-4733
72. LaLonde R.L., Sherry B.D., Kang E.J., and Toste F.D. J. Am. Chem. Soc. 129 (2007) 2452-2453
73. Zhang Z.B., Bender C.F., and Widenhoefer R.A. Org. Lett. 9 (2007) 2887-2889
74. Zhang Z.B., Bender C.F., and Widenhoefer R.A. J. Am. Chem. Soc. 129 (2007) 14148-14149
75. Morita N., and Krause N. Eur. J. Org. Chem. (2006) 4634-4641
76. Patil N.T., Lutete L.M., Nishina N., and Yamamoto Y. Tetrahedron Lett. 47 (2006) 4749-4751
77. Hoover J.M., Petersen J.R., Pikul J.H., and Johnson A.R. Organometallics 23 (2004) 4614-4620
78. Abdel-Magid A.F., Maryanoff C.A., and Carson K.G. Tetrahedron Lett. 39 (1990) 5595-5598
79. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
80. Ho C.K., Schuler A.D., Yoo C.B., Herron S.R., Kantardjieff K.A., and Johnson A.R. Inorg. Chim. Acta 341 (2002) 71-76
81. Jonasson C., Horváth A., and Bäckvall J.-E. J. Am. Chem. Soc. 122 (2000) 9600-9609
82. Petersen J.R., Hoover J.M., Kassel W.S., Rheingold A.L., and Johnson A.R. Inorg. Chim. Acta 358 (2005) 687-694
83. Perrin D.D., and Armarego L.F. Purification of Laboratory Chemicals (1988), Pergamon Press, New York