Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component List-Barbas-Mannich reaction

Journal of the American Chemical Society

Volumn 125, Issue 37, 2003, Pages 11208-11209

  Hayashi, Yujiro ^a   Tsuboi, Wataru ^a   Shoji, Mitsuru ^a   Suzuki, Noriyuki ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; FREEZING; PRESSURE; TECHNIQUE; TEMPERATURE;

EID: 0043194285     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0372513     Document Type: Article

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27. There are several reports describing the relationship between enantioselectivity and pressure in asymmetric catalytic reactions. (a) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241. (b) Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (d) Tietze, L. F.; Ott, C.; Frey, U. Liebigs Ann. 1996, 63. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
28. There are several reports describing the relationship between enantioselectivity and pressure in asymmetric catalytic reactions. (a) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241. (b) Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (d) Tietze, L. F.; Ott, C.; Frey, U. Liebigs Ann. 1996, 63. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
29. There are several reports describing the relationship between enantioselectivity and pressure in asymmetric catalytic reactions. (a) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241. (b) Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (d) Tietze, L. F.; Ott, C.; Frey, U. Liebigs Ann. 1996, 63. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
30. There are several reports describing the relationship between enantioselectivity and pressure in asymmetric catalytic reactions. (a) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241. (b) Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (d) Tietze, L. F.; Ott, C.; Frey, U. Liebigs Ann. 1996, 63. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
31. There are several reports describing the relationship between enantioselectivity and pressure in asymmetric catalytic reactions. (a) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241. (b) Marko, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015. (c) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271. (d) Tietze, L. F.; Ott, C.; Frey, U. Liebigs Ann. 1996, 63. (e) Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599. (f) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
32. Hayashi, Y.; Tsuboi, W. Unpublished work.
33. The p-methoxyphenyl protecting group on an amine can be easily removed by oxidation with CAN. See ref 4b.
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