Unexpected catalytic behavior of chiral bisoxazoline in asymmetric reaction of lithium ester enolate with imine

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 5, 1999, Pages 720-721

  Kambara, Takeshi ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric reactions; Catalysis; Enolates; Oxazolines

Indexed keywords

BENZALDEHYDE DERIVATIVE; BETA LACTAM; BISOXAZOLINE; ESTER DERIVATIVE; IMINE; LIGAND; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; POLYMERIZATION; REACTION ANALYSIS; STOICHIOMETRY; TEMPERATURE;

EID: 0033040001     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.720     Document Type: Article

References (17)

1. Franklin A. S., Paterson I., Contemporary Organic Synthesis, 1994, 317.
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," John Wiley and Sons, Inc., New York, 1995.
3. 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," John Wiley and Sons, Inc., New York, 1995.
4. 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," John Wiley and Sons, Inc., New York, 1995.
5. For the recently reported asymmetric alkylation of ester enolate, see: Matsuo J., Kobayashi S., Koga K., Tetrahedron Lett., 39, 9723-9726 (1998).
6. Shindo M., Koga K., Tomioka K., J. Org. Chem., 63, 9351-9357 (1998).
7. For the catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani H., Ueno M., Kobayashi S., J. Am. Chem. Soc., 119, 7153-7154 (1997); Warrener R. N., Liu L., Russell R. A., Chem. Commun., 2173-2174 (1997); Hagiwara E., Fujii A., Sodeoka M., J. Am. Chem. Soc., 120, 2474-2475 (1998); Ferraris D., Young B., Dudding T., Lectka T., J. Am. Chem. Soc., 120, 4548-4549 (1998).
8. For the catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani H., Ueno M., Kobayashi S., J. Am. Chem. Soc., 119, 7153-7154 (1997); Warrener R. N., Liu L., Russell R. A., Chem. Commun., 2173-2174 (1997); Hagiwara E., Fujii A., Sodeoka M., J. Am. Chem. Soc., 120, 2474-2475 (1998); Ferraris D., Young B., Dudding T., Lectka T., J. Am. Chem. Soc., 120, 4548-4549 (1998).
9. For the catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani H., Ueno M., Kobayashi S., J. Am. Chem. Soc., 119, 7153-7154 (1997); Warrener R. N., Liu L., Russell R. A., Chem. Commun., 2173-2174 (1997); Hagiwara E., Fujii A., Sodeoka M., J. Am. Chem. Soc., 120, 2474-2475 (1998); Ferraris D., Young B., Dudding T., Lectka T., J. Am. Chem. Soc., 120, 4548-4549 (1998).
10. For the catalytic addition reaction of ester enolate equivalents with imines, see: Ishitani H., Ueno M., Kobayashi S., J. Am. Chem. Soc., 119, 7153-7154 (1997); Warrener R. N., Liu L., Russell R. A., Chem. Commun., 2173-2174 (1997); Hagiwara E., Fujii A., Sodeoka M., J. Am. Chem. Soc., 120, 2474-2475 (1998); Ferraris D., Young B., Dudding T., Lectka T., J. Am. Chem. Soc., 120, 4548-4549 (1998).
11. Fujieda H., Kanai M., Kambara T., Iida A., Tomioka, K., J. Am. Chem. Soc., 119, 2060-2061 (1997); Kambara T., Hussein M. A., Fujieda H., Iida A., Tomioka K., Tetrahedron Lett., 39, 9055-9058 (1998).
12. Fujieda H., Kanai M., Kambara T., Iida A., Tomioka, K., J. Am. Chem. Soc., 119, 2060-2061 (1997); Kambara T., Hussein M. A., Fujieda H., Iida A., Tomioka K., Tetrahedron Lett., 39, 9055-9058 (1998).
13. For the application of Box ligand in asymmetric reaction of organolithium with imine, see: Denmark S. E., Nicaise O. J.-C., J. Chem. Soc., Chem. Commun., 999-1004 (1996).
14. Corey E. J., Imai N., Zhang H.-U., J. Am. Chem. Soc., 113, 728-729 (1991); Pfaltz A., Acc. Chem. Res., 26, 339-345 (1993).
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16. The ee and absolute configuration were determined as described in ref. 6.
17. Involvement of the Box ligand 2a and the lithium enolate 3b in a ratio of 1: over 2 may not be ruled out at the present time.