Formation of Optically Active Functionalized β-Hydroxy Nitrones Using a Proline Catalyzed Aldol Reaction of Aldehydes with Carbonyl Compounds and Hydroxylamines

Synlett

Volumn , Issue 12, 2003, Pages 1915-1918

  Bøgevig, Anders ^a   Poulsen, Thomas B ^a   Zhuang, Wei ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric catalysis; Carbonyl compounds; Hydroxylamines; L proline; Nitrones

Indexed keywords

ALDEHYDE DERIVATIVE; BENZYL[3,3 BIS(ETHOXYCARBONYL) 2 ETHYL 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; BENZYL[3,3 BIS(ETHOXYCARBONYL) 2 ISOPROPYL 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; BENZYL[3,3 BIS(ETHOXYCARBONYL) 2 METHYL 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; CARBONYL DERIVATIVE; HYDROXYLAMINE; NITRONE DERIVATIVE; PROLINE; TERT BUTYL(3 ETHOXYCARBONYL 4,4,4 TRIFLUORO 2 METHYL 3 HYDROXYBUTYLIDENE)AMINE N OXIDE; TERT BUTYL[3,3 BIS(ETHOXYCARBONYL) 2 (2 ALLYL) 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; TERT BUTYL[3,3 BIS(ETHOXYCARBONYL) 2 ETHYL 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; TERT BUTYL[3,3 BIS(ETHOXYCARBONYL) 2 METHYL 3 HYDROXYPROPYLIDENE]AMINE N OXIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; OPTICS; REACTION ANALYSIS;

EID: 0142091316     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41479     Document Type: Article

References (61)

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38. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
39. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
40. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
41. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
42. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
43. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
44. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
45. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
46. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
47. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
48. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
49. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
50. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
51. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
52. See for example: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223. (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233. (d) Horstmann, T. E. ; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635; Angew. Chem. 2000, 112, 3781. (e) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975. (f) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441. (g) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737. (h) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. (i) Enders, D.; Seki, A. Synlett 2002, 26. (j) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611. (k) Brunner, H.; Krumey, C. J. Mol. Catal A 1999, 142, 7. (l) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (m) Halland, N.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331. (n) Halland, N.; Aburel, S. P.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 661. (o) Melchiorre, P.; Jørgensen, K. A. Org. Chem. 2003, 68, 4151. (p) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, in press.
53. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
54. See for example: (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J. III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831. (b) Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653.
55. See for example: (a) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J. III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831. (b) Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 11653.
56. For leading references to the synthesis of trifluoromethyl containing compounds and their applications, see for example: (a) Lin, P.; Liang, J. Tetrahedron 2000, 56, 3635. (b) Solohonok, V. A. Enantiocontrolled Synthesis of Fluoro- Organic Compounds, Stereochemical Challenges and Biomedical Targets; John Wiley and Sons: New York, 1999. (c) Organofluorine Chemistry - Principles and Commercial Application; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (d) Fluorine-Containing Molecules, Structure, Reactivity, Synthesis and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Eds.; VCH Publishers: Weinheim, 1998.
57. For leading references to the synthesis of trifluoromethyl containing compounds and their applications, see for example: (a) Lin, P.; Liang, J. Tetrahedron 2000, 56, 3635. (b) Solohonok, V. A. Enantiocontrolled Synthesis of Fluoro- Organic Compounds, Stereochemical Challenges and Biomedical Targets; John Wiley and Sons: New York, 1999. (c) Organofluorine Chemistry - Principles and Commercial Application; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (d) Fluorine-Containing Molecules, Structure, Reactivity, Synthesis and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Eds.; VCH Publishers: Weinheim, 1998.
58. For leading references to the synthesis of trifluoromethyl containing compounds and their applications, see for example: (a) Lin, P.; Liang, J. Tetrahedron 2000, 56, 3635. (b) Solohonok, V. A. Enantiocontrolled Synthesis of Fluoro- Organic Compounds, Stereochemical Challenges and Biomedical Targets; John Wiley and Sons: New York, 1999. (c) Organofluorine Chemistry - Principles and Commercial Application; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (d) Fluorine-Containing Molecules, Structure, Reactivity, Synthesis and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Eds.; VCH Publishers: Weinheim, 1998.
59. For leading references to the synthesis of trifluoromethyl containing compounds and their applications, see for example: (a) Lin, P.; Liang, J. Tetrahedron 2000, 56, 3635. (b) Solohonok, V. A. Enantiocontrolled Synthesis of Fluoro- Organic Compounds, Stereochemical Challenges and Biomedical Targets; John Wiley and Sons: New York, 1999. (c) Organofluorine Chemistry - Principles and Commercial Application; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994. (d) Fluorine-Containing Molecules, Structure, Reactivity, Synthesis and Applications; Liebman, J. F.; Greenberg, A.; Dolbier, W. R., Eds.; VCH Publishers: Weinheim, 1998.
60. For preparation of nitrones from aldehydes and ketones, see for example: (a) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537. (b) Tranco, S.; Merchan, F. L.; Merino, P. Synth. Commun. 1995, 25, 2275.
61. For preparation of nitrones from aldehydes and ketones, see for example: (a) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537. (b) Tranco, S.; Merchan, F. L.; Merino, P. Synth. Commun. 1995, 25, 2275.