A simple and efficient L-prolinamide-catalyzed α-selenenylation reaction of aldehydes

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2817-2820

  Wang, Wei ^a   Wang, Jian ^a   Li, Hao ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMIDE; PROLINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 4344625961     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0488946     Document Type: Article

References (43)

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22. We recently developed novel pyrrolidine sulfonamides (their structures are shown in Table 1, entries 3 and 4) as organocatalysts for catalyzing asymmetric α-aminoxylation and the Mannich-type reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2004, submitted for publication. (b) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, submitted for publication. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (d) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
23. We recently developed novel pyrrolidine sulfonamides (their structures are shown in Table 1, entries 3 and 4) as organocatalysts for catalyzing asymmetric α-aminoxylation and the Mannich-type reactions: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2004, submitted for publication. (b) Wang, W.; Wang, J.; Li, H. Tetrahedron Lett. 2004, submitted for publication. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (d) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
24. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
25. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (d) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
26. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (d) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
27. For proline-catalyzed aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (b) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (d) Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152.
28. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
29. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
30. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
31. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
32. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
33. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
34. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
35. For proline-catalyzed Mannich reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (b) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827. (c) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (d) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (e) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923. (f) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas. C. F., III. J. Org. Chem. 2003, 68, 9624. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
36. For proline-catalyzed α-amination reactions, see: (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (b) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
37. For proline-catalyzed α-amination reactions, see: (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (b) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
38. For proline-catalyzed α-aminoxylation reactions, see: (a) Brown, F. J.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (b) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (c) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
39. For proline-catalyzed α-aminoxylation reactions, see: (a) Brown, F. J.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (b) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (c) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
40. For proline-catalyzed α-aminoxylation reactions, see: (a) Brown, F. J.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (b) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (c) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
41. For proline-catalyzed α-aminoxylation reactions, see: (a) Brown, F. J.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (b) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (c) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112.
42. Recently, Jørgensen and co-workers reported L-prolinamide- catalyzed α-ehlorination of ketones: Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
43. L-Proline and L-prolinamide exhibited no enantioselectivity on the α-selenenylation of isovaleraldehyde. However, our pyrrolidine tosyl sulfonamide (its structure is shown in Table 1, entry 4) provided 60% ee.