Synthesis of enantiomerically pure 3-amino-1,2-diols by reductive amination of racemic 2,3-dialkoxyketones

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8277-8280

  Hutin, Pierre ^a   Petit, Yves ^a   Larchevêque, Marc ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA METHYLBENZYLAMINE; BORANE DERIVATIVE; KETONE;

AMINATION; ARTICLE; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032487788     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01856-5     Document Type: Article

References (30)

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3. 3. for some recent syntheses, see: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722; Veith, U.; Schwardt, O.; Jäger, V. Synlett, 1996, 1181-1183; Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron:Asymmetry 1996, 7, 1169-1180; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, 1997, 634-642; Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. J. Amer. Chem. Soc. 1997, 119, 3179-3180.
4. 3. for some recent syntheses, see: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722; Veith, U.; Schwardt, O.; Jäger, V. Synlett, 1996, 1181-1183; Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron:Asymmetry 1996, 7, 1169-1180; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, 1997, 634-642; Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. J. Amer. Chem. Soc. 1997, 119, 3179-3180.
5. 3. for some recent syntheses, see: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722; Veith, U.; Schwardt, O.; Jäger, V. Synlett, 1996, 1181-1183; Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron:Asymmetry 1996, 7, 1169-1180; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, 1997, 634-642; Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. J. Amer. Chem. Soc. 1997, 119, 3179-3180.
6. 3. for some recent syntheses, see: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722; Veith, U.; Schwardt, O.; Jäger, V. Synlett, 1996, 1181-1183; Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron:Asymmetry 1996, 7, 1169-1180; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, 1997, 634-642; Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. J. Amer. Chem. Soc. 1997, 119, 3179-3180.
7. 3. for some recent syntheses, see: Overhand, M.; Hecht, S.M. J. Org. Chem. 1994, 59, 4721-4722; Veith, U.; Schwardt, O.; Jäger, V. Synlett, 1996, 1181-1183; Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron:Asymmetry 1996, 7, 1169-1180; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, 1997, 634-642; Du Bois, J.; Tomooka, C.S.; Hong, J.; Carreira, E.M. J. Amer. Chem. Soc. 1997, 119, 3179-3180.
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16. 6. Yamamoto, Y.; Komatsu, T.; Maruyama, K. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y. J. Chem. Soc., Chem. Commun. 1989, 930-931; Clark, R.D.; Jahangir; Souchet, M.; Kern, J.R. J. Chem. Soc., Chem. Commun. 1985, 814-815; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 31, 4175-4176; Cainelli, G.; Giacomini, D.; Mezzina, E.; Panunzio, M.; Zarantonello, Tetrahedron Lett. 1991, 32, 2967-2970; Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.M.; Peters, K.; von Schnering, H.G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1298-1301; Cativiela, C.; Diaz-de-Villegas, M.D., Galvez, J.A. Tetrahedron Lett. 1995, 36, 2859-2862; Solladié-Cavallo, A.; Bonne, F. Tetrahedron:Asymmetry 1996, 7, 171-180; Razavi, H.; Polt, R. Tetrahedron Lett. 1998, 39, 3371-3374.
17. 6. Yamamoto, Y.; Komatsu, T.; Maruyama, K. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y. J. Chem. Soc., Chem. Commun. 1989, 930-931; Clark, R.D.; Jahangir; Souchet, M.; Kern, J.R. J. Chem. Soc., Chem. Commun. 1985, 814-815; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 31, 4175-4176; Cainelli, G.; Giacomini, D.; Mezzina, E.; Panunzio, M.; Zarantonello, Tetrahedron Lett. 1991, 32, 2967-2970; Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.M.; Peters, K.; von Schnering, H.G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1298-1301; Cativiela, C.; Diaz-de-Villegas, M.D., Galvez, J.A. Tetrahedron Lett. 1995, 36, 2859-2862; Solladié-Cavallo, A.; Bonne, F. Tetrahedron:Asymmetry 1996, 7, 171-180; Razavi, H.; Polt, R. Tetrahedron Lett. 1998, 39, 3371-3374.
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25. 13. The stereochemistry was determined by NMR after transformation of compounds 7 into aziridines: (equation presented)
26. 14. Knupp, G.; Frahm, A.W. Chem. Ber. 1984, 117, 2076-2098; Lauktien, G.; Volk, F.J.; Frahm, A.W. Tetrahedron:Asymmetry 1997, 8, 3457-3466; Bisel, P.; Breitling, E.; Frahm, A.W. Eur. J. Org. Chem. 1998, 729-733.
27. 14. Knupp, G.; Frahm, A.W. Chem. Ber. 1984, 117, 2076-2098; Lauktien, G.; Volk, F.J.; Frahm, A.W. Tetrahedron:Asymmetry 1997, 8, 3457-3466; Bisel, P.; Breitling, E.; Frahm, A.W. Eur. J. Org. Chem. 1998, 729-733.
28. 14. Knupp, G.; Frahm, A.W. Chem. Ber. 1984, 117, 2076-2098; Lauktien, G.; Volk, F.J.; Frahm, A.W. Tetrahedron:Asymmetry 1997, 8, 3457-3466; Bisel, P.; Breitling, E.; Frahm, A.W. Eur. J. Org. Chem. 1998, 729-733.
29. 15. A, B, and C were minimized using AM1 semi-empirical method and Polak-Ribiere algorithm (conjugate gradient) as released in Hyperchem 2.0 with a RMS gradient of 0.02 kcal/(mol.Å)
30. 3).