Novel approach for asymmetric synthesis of fluorinated β-amino sulfones and allylic amines

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2707-2710

  Fustero, Santos ^a   García Soler, Juan ^a   Bartolomé, Ana ^a   Sánchez Roselló, María ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; CHLORIDE; SULFONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; FLUORINATION; METHYLATION; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TECHNIQUE;

ALLYL COMPOUNDS; AMINES; HYDROCARBONS, FLUORINATED; STEREOISOMERISM; SULFONES;

EID: 0141520374     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034892u     Document Type: Article

References (45)

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28. -1): imino (Z)-(S)-3a 0.0; imino (E)-(S)-3a 10.7; enamino (Z)-(S)-3a 9.2].
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30. For reviews, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685-700. (c) Stütz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328. For other recent examples, see: (d) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762. (e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (f) Katritzky, A. R.; Cheng, D.; Li, J. J. Org. Chem. 1998, 63, 3438-3444.
31. For reviews, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685-700. (c) Stütz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328. For other recent examples, see: (d) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762. (e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (f) Katritzky, A. R.; Cheng, D.; Li, J. J. Org. Chem. 1998, 63, 3438-3444.
32. For reviews, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685-700. (c) Stütz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328. For other recent examples, see: (d) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762. (e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (f) Katritzky, A. R.; Cheng, D.; Li, J. J. Org. Chem. 1998, 63, 3438-3444.
33. For reviews, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685-700. (c) Stütz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328. For other recent examples, see: (d) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762. (e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (f) Katritzky, A. R.; Cheng, D.; Li, J. J. Org. Chem. 1998, 63, 3438-3444.
34. For reviews, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685-700. (c) Stütz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328. For other recent examples, see: (d) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762. (e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (f) Katritzky, A. R.; Cheng, D.; Li, J. J. Org. Chem. 1998, 63, 3438-3444.
35. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
36. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
37. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
38. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
39. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
40. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
41. For racemic synthesis, see: (a) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem. 1966, 78, 640-640; Angew. Chem., Int. Ed. Engl. 1966, 5, 600-600. (b) Bégué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Synlett 1995, 659-660. (c) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134-2137. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77-78. (e) Sergeeva, N. N.; Golubev, A. S.; Hennig, L.; Findeisen, M.; Paetzold, E.; Oehme, G.; Burger, K. J. Fluorine Chem. 2001, 111, 41-44. (f) Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M. Org. Lett. 2002, 4, 769-772.
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