The First Catalytic Asymmetric Addition of Dialkylzincs to α-Ketoesters

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3781-3784

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

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ESTERS; KETONES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 0013130960     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026315w     Document Type: Article

References (34)

1. For reviews of the enantioselective construction of quaternary centers, see: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Corey, E. J.; Guzman-Peresz, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (c) Christoffers, S.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
2. For reviews of the enantioselective construction of quaternary centers, see: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Corey, E. J.; Guzman-Peresz, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (c) Christoffers, S.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
3. For reviews of the enantioselective construction of quaternary centers, see: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460. (b) Corey, E. J.; Guzman-Peresz, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. Christoffers, S.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
4. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis: VCH: Weinhein, Germany, 1997.
5. (a) Sugimura, H.; Watanabe, T. Synlett 1994, 175-177.
6. (b) Tamai, Y.; Nakano, T.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 1994, 439-445.
7. Akiyama, T.; Nishimoto, H.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1992, 447-450.
8. Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
9. (e) Boireau, G.; Deberly, A.; Loupy, A.; Monteux, D. Tetrahedron Lett. 1999, 40, 6919-6922.
10. (f) Loupy, A.; Monteux, D. A. Tetrahedron 2002, 58, 1541-1549 and references therein.
11. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
12. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
13. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
14. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
15. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
16. Methods that use ≥ 1 equiv of chiral ligand in the enantioselective alkylation of α-ketoesters have been developed, but few (see 4e) 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. 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. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711-713.
17. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
18. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
19. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
20. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
21. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
22. Mukaiyama aldol: (a) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699. Isocyanoacetates: (b) Ito, Y.; Sawamura, M.; Hamashima, H.; Emura, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681-4684. Self-aldol: Juhl, K.; Gathergood, N.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 2000, 2211-2212. [2 + 2]-Cycloaddition: Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125-2128. Hetero-Diels-Alder: (e) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233. Friedel-Crafts: (f) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 160-163.
23. For reviews, see: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824. (b) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 911-922.
24. For reviews, see: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824. (b) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 911-922.
25. 2Zn: (b) Ramon, D. J.; Yus, M. Tetrahedron 1998, 54, 5651-5666. Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971.
26. 2Zn: (b) Ramon, D. J.; Yus, M. Tetrahedron 1998, 54, 5651-5666. Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971.
27. 2Zn: (b) Ramon, D. J.; Yus, M. Tetrahedron 1998, 54, 5651-5666. Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970-10971.
28. For an example of this problem, see ref 3a. Diastereoselective additions to α-ketoesters are often limited to MeMgX and ArMgX which do not contain β-hydrogens (see ref 3b-d).
29. 2Et at -10 °C gives 19% reduction and 60% addition.
30. DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2001, 3, 3053-3056.
31. We had found that bifunctional Lewis acid-Lewis base salen catalysts were much more reactive compared to the Noyori DAIB catalysts (see ref 9). Under comparable conditions, these salen catalysts have among the fastest rates (catalytic in titanium) for the enantioselective addition of dialkylzincs to aldehydes. Separation of the Lewis acid and Lewis base sites in these salen catalysts, which is not possible in the DAIB-type catalyst, is proposed to account for these rate differences
32. (a) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron, 1997, 53, 14327-14338.
33. (b) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740.
34. We thank Prof. Patrick Walsh for a sample of titanium tetra[(S)-1-(4-methylphenyl)propoxide]: Davis, T. J.; Balsells, J.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2001, 3, 2161-2164.