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For recent representative examples of C-H activation, see: (a) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995. (b) Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358. (c) Johnson, J. A.; Li, N.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900. (d) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. (e) Karig, G.; Moon, M.-T.; Thasana, N.; Gallagher, T. Org. Lett. 2002, 4, 3115. (f) Saaby, S.; Bayon, P.; Aburel, P. S.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 4352. (g) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202. (h) Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378.
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For reviews and recent references on the catalytic asymmetric Mannich reaction, see: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (d) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (f) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (h) Juhl, K.; Gathergood, N.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (i) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (j) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (k) List, B. Synlett 2001, 1675.
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For reviews and recent references on the catalytic asymmetric Mannich reaction, see: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (d) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (f) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (h) Juhl, K.; Gathergood, N.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (i) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (j) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (k) List, B. Synlett 2001, 1675.
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For reviews and recent references on the catalytic asymmetric Mannich reaction, see: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060. (d) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090. (e) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (f) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842. (g) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857. (h) Juhl, K.; Gathergood, N.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (i) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (j) List, B. J. Am. Chem. Soc. 2000, 122, 9336. (k) List, B. Synlett 2001, 1675.
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For other approaches to the asymmetric synthesis of threo-methylphenidate. see: (a) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J. Med. Chem. 1998, 41, 591. (b) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750. (c) Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T. Org. Lett. 1999, 1, 175.
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For other approaches to the asymmetric synthesis of threo-methylphenidate. see: (a) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J. Med. Chem. 1998, 41, 591. (b) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750. (c) Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T. Org. Lett. 1999, 1, 175.
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4 as compared to those of Winkler's study (ref 17) is uncertain. Winkler, however, reported the de for 6b after chromatographic purification of the initial Boc-protected product and trituration of the HCl salt of 6b, which could have led to diastereomeric enrichment.
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0038412929
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note
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4-catalyzed reaction with the (3R)-substituted prolines.
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