L-proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric aldol reactions

Tetrahedron Letters

Volumn 43, Issue 48, 2002, Pages 8741-8743

  Loh, Teck Peng ^a   Feng, Li Chun ^b   Yang, Hai Yan ^a   Yang, Jian Ying ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; PROLINE;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; IONIZATION; LIQUID;

EID: 0037175484     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02104-4     Document Type: Article

References (16)

1. Trost B.M. Science. 254:1991;1471.
2. Trost B.M. Angew. Chem., Int. Ed. Engl. 34:1995;259.
3. For early use of L-proline as a catalyst of the Hajos-Eder-Sauer-Wiechert reaction, see: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615; (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496; (c) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358.
4. For early use of L-proline as a catalyst of the Hajos-Eder-Sauer-Wiechert reaction, see: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615; (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496; (c) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358.
5. For early use of L-proline as a catalyst of the Hajos-Eder-Sauer-Wiechert reaction, see: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615; (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496; (c) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358.
6. List B., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 122:2000;2395.
7. Notz W., List B. J. Am. Chem. Soc. 122:2000;7386.
8. Sakthivel K., Notz W., Bui T., Barbas C.F. III. J. Am. Chem. Soc. 123:2001;5260.
9. For a direct asymmetric aldol reaction catalyzed by heterobimetallic bifunctional Lewis acid/Brønsted base, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871; (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561; (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003; (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
10. For a direct asymmetric aldol reaction catalyzed by heterobimetallic bifunctional Lewis acid/Brønsted base, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871; (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561; (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003; (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
11. For a direct asymmetric aldol reaction catalyzed by heterobimetallic bifunctional Lewis acid/Brønsted base, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871; (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561; (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003; (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
12. For a direct asymmetric aldol reaction catalyzed by heterobimetallic bifunctional Lewis acid/Brønsted base, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871; (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561; (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003; (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
13. For a direct asymmetric aldol reaction catalyzed by heterobimetallic bifunctional Lewis acid/Brønsted base, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871; (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561; (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (d) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003; (e) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
14. Wasserscheid P., Keim W. Angew. Chem., Int. Ed. Engl. 39:2000;3772. and references cited therein.
15. Zhao D.B., Wu M., Kou Y., Min E. Catal. Today. 74:2002;157.
16. Sheldon R. Chem. Commun. 2001;2399. and references cited therein.