Design, synthesis, and application of a C2 symmetric chiral ligand for enantioselective conjugate addition of organolithium to α,β-unsaturated aldimine

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9351-9357

  Shindo, Mitsuru ^a   Koga, Kenji ^b   Tomioka, Kiyoshi ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIMETHOXY 1,2 DIPHENYLETHANE; ALPHA,BETA ALDIMINE; ETHANE; IMINE; LIGAND; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CONJUGATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032509540     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813181     Document Type: Article

References (78)

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58. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
59. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
60. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
61. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
62. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
63. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
64. Chiral external ligand controlled 1,2-addition of organolithium to imines has been another interesting kind of chemistry, see: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681. (b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 1603. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165. (g) Tomioka, K.; Satoh, M.; Taniyama, D.; Kanai, M.; Iida, A. Heterocycles 1998, 47, 77. For review, see: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
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