Development of bifunctional salen catalysts: Rapid, chemoselective alkylations of α-ketoesters

Journal of the American Chemical Society

Volumn 124, Issue 43, 2002, Pages 12668-12669

  DiMauro, Erin F ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA KETOESTER; ESTER DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHEMOSENSITIVITY; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 0037202209     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026498h     Document Type: Article

References (25)

1. DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2001, 3, 3053-3056.
2. (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
3. (b) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 911-922.
4. MIB: Nugent, W. A. J. Chem. Soc., Chem. Commun. 1999, 1369-1370.
5. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinhein, 1997.
6. For example, we have found that addition of EtMgBr to α-ketoesters affords significant amounts (16-63%) of the reduction product (see Supporting Information).
7. For other examples of this problem, see: (a) Sugimura, H.; Watanabe, T. Synlett 1994, 175-177. Diastereoselective additions to α-ketoesters are often limited to MeMgX and ArMgX which do not contain β-hydrogens. (b) Tamai, Y.; Nakano, T.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 439-445. (c) Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447-450. (d) Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
8. For other examples of this problem, see: (a) Sugimura, H.; Watanabe, T. Synlett 1994, 175-177. Diastereoselective additions to α-ketoesters are often limited to MeMgX and ArMgX which do not contain β-hydrogens. (b) Tamai, Y.; Nakano, T.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 439-445. (c) Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447-450. (d) Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
9. For other examples of this problem, see: (a) Sugimura, H.; Watanabe, T. Synlett 1994, 175-177. Diastereoselective additions to α-ketoesters are often limited to MeMgX and ArMgX which do not contain β-hydrogens. (b) Tamai, Y.; Nakano, T.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 439-445. (c) Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447-450. (d) Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
10. For other examples of this problem, see: (a) Sugimura, H.; Watanabe, T. Synlett 1994, 175-177. Diastereoselective additions to α-ketoesters are often limited to MeMgX and ArMgX which do not contain β-hydrogens. (b) Tamai, Y.; Nakano, T.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 439-445. (c) Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447-450. (d) Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
11. No enantioselection was seen in a prior DAIB α-ketoester alkylation: Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19-37.
12. For examples of salen-Zn complexes, see: (a) Morris, G. A.; Zhou, H.; Stern, C. L.; Nguyen, S. T. Inorg. Chem. 2001, 40, 3222-3227. (b) Singer, A. L.; Atwood, D. A. Inorg. Chim. Acta 1998, 277, 157-162.
13. For examples of salen-Zn complexes, see: (a) Morris, G. A.; Zhou, H.; Stern, C. L.; Nguyen, S. T. Inorg. Chem. 2001, 40, 3222-3227. (b) Singer, A. L.; Atwood, D. A. Inorg. Chim. Acta 1998, 277, 157-162.
14. For examples of salen-Mg complexes, see: Corazza, F.; Floriani, C.; Chiesi-Villa, A.; Guastini, C.; Ciurli, S. J. Chem. Soc., Dalton Trans. 1988, 2341-2345.
15. 2 complexes, see: (a) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327-14338. (b) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko. M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 1293-1295. (c) Chen, H.; White, P. S.; Gagne, M. R. Organometallics 1998, 17, 5358-5366.
16. 2 complexes, see: (a) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327-14338. (b) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko. M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 1293-1295. (c) Chen, H.; White, P. S.; Gagne, M. R. Organometallics 1998, 17, 5358-5366.
17. 2 complexes, see: (a) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327-14338. (b) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko. M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 1293-1295. (c) Chen, H.; White, P. S.; Gagne, M. R. Organometallics 1998, 17, 5358-5366.
18. We have also obtained a crystal structure for an analogue of 8 which demonstrates that coordination of the amine base to the Ti does not occur.
19. Seebach, D.; Marti, R. E., Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740.
20. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
21. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
22. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
23. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
24. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
25. Methods that use ≥1 equiv chiral ligand for enantioselective ≤-ketoester alkylation are known, but few (see 13e) are synthetically useful. (a) Abenhaim, D.; Boireau, G.; Sabourault, B. Tetrahedron Lett. 1980, 21, 3043-3046. (b) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597-1606. (c) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. (d) Zadel, G.; Breitmaier, E. Chem. Ber. 1994, 127, 1323-1326. (e) Yamada, K.; Tozawa, T.; Nishida, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 2301-2308. (f) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.