A factor affecting enantioselective reaction of a ternary complex of lithium ester enolate with imine

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9055-9058

  Kambara, Takeshi ^b   Hussein, Mostafa Ahmed ^b   Fujieda, Hiroki ^a   Iida, Akira ^b   Tomioka, Kiyoshi ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; IMINE; LITHIUM DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0032481071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02053-X     Document Type: Article

References (17)

1. 1. Caine, D. in Carbon-Carbon Bond Formation Augustine, R. L. Ed. Marcel Dekker, Inc. New York, 1979, p. 85; Franklin, A. S.; Paterson, I. Contemporary Organic Synthesis 1994, 317.
2. 1. Caine, D. in Carbon-Carbon Bond Formation Augustine, R. L. Ed. Marcel Dekker, Inc. New York, 1979, p. 85; Franklin, A. S.; Paterson, I. Contemporary Organic Synthesis 1994, 317.
3. 2. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis 1995, John Wiley and Sons, Inc., New York.
4. 2. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis 1995, John Wiley and Sons, Inc., New York.
5. 2. Tomioka, K. Synthesis 1990, 541-549; Noyori, R. Asymmetric Catalysis in Organic Synthesis John Wiley and Sons, Inc. New York, 1994; Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis 1995, John Wiley and Sons, Inc., New York.
6. 3. Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060-2061.
7. 4. For the recently reported catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997; 119, 7153-7154; Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
8. 4. For the recently reported catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997; 119, 7153-7154; Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
9. 5. Lithium ester enolate was generated by treatment with 2.2 equiv of the lithium amide.
10. 6. All new compounds described herein gave satisfactory analytical and spectroscopic data.
11. 7. Daicel Chiralcel OD-H, i-PrOH/hexane = 1/50.
12. 3). Ee was determined by HPLC analysis to be 92% (Daicel Chiralcel OD-H, hexane-iPrOH (50:1), 0.5 mL/min, 250 nm, 22 min (R) : 27 min (S)). The chiral ligand 1 was recovered through column chromatography for reuse quantitatively.
13. 9. Prepared by the reaction of the corresponding trimethylsilyl enol ether with benzaldehyde imine in the presence of zinc iodide.
14. 10. Prepared by the reaction of methanolysis of 4a of 99% ee, enantioenriched by recrystallization of 4a of 88% ee, and following HCl catalyzed transesterification with 3-pentanol.
15. 11. Chen, L.-Y.; Zaks, A.; Chackalamannil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343; McKittrick, B. A.; Ma, K.; Dugar, S. Clader, J. W.; Davis, Jr., H.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1947-1950; Wu, G.; Tormos, W. J. Org. Chem. 1997, 62, 6412-6414.
16. 11. Chen, L.-Y.; Zaks, A.; Chackalamannil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343; McKittrick, B. A.; Ma, K.; Dugar, S. Clader, J. W.; Davis, Jr., H.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1947-1950; Wu, G.; Tormos, W. J. Org. Chem. 1997, 62, 6412-6414.
17. 11. Chen, L.-Y.; Zaks, A.; Chackalamannil, S.; Dugar, S. J. Org. Chem. 1996, 61, 8341-8343; McKittrick, B. A.; Ma, K.; Dugar, S. Clader, J. W.; Davis, Jr., H.; Czarniecki, M. Bioorg. Med. Chem. Lett. 1996, 6, 1947-1950; Wu, G.; Tormos, W. J. Org. Chem. 1997, 62, 6412-6414.