Chiral 2,6-Bis(oxazolinyl)pyridine-rare earth metal complexes as catalysts for highly enantioselective 1,3-dipolar cycloaddition reactions of 2-Benzopyrylium-4-olates

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 47-56

  Suga, Hiroyuki ^a   Inoue, Kei ^a   Inoue, Shuichi ^a   Kakehi, Akikazu ^a   Shiro, Motoo ^b  

^a SHINSHU UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETONE; CATALYSIS; CATALYSTS; COMPLEXATION; DECOMPOSITION; ESTERS; PH EFFECTS; REACTION KINETICS;

ENANTIOSELECTIVITIES; EXO-CYCLOADDUCT; LEWIS ACID CATALYSTS; TRIFLUOROACETIC ACID;

RARE EARTH ELEMENTS;

2 BENZOPYRYLIUM 4 OLATE; 2,6 BIS(OXAZOLINYL)PYRIDINE; ACETOPHENONE DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA KETO ESTER; BENZENE DERIVATIVE; CARBENOID; ESTER DERIVATIVE; METAL COMPLEX; O METHOXYCARBONYL ALPHA DIAZOACETOPHENONE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DECOMPOSITION; DIASTEREOISOMER; ENANTIOSELECTIVITY;

BIOLOGICAL FACTORS; CATALYSIS; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; METALS, RARE EARTH; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIDINES; RHODIUM; SCANDIUM; YTTERBIUM;

EID: 11844286891     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049007f     Document Type: Article

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70. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
71. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
72. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
73. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
74. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
75. For recent examples using rare earth metal triflate-Pybox complexes as chiral Lewis acid, see: (a) Schaus, S. C.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001. (b) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 129095. (d) Evans, D. A.; Masse, C. E.; Wu, J. Org. Lett. 2002, 4, 3375. (e) Evans, D. A.; Wu, J.; Masse, C. E.; MacMillan, D. W. C. Org. Lett. 2002, 4, 3379. (f) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10162. (g) Evans, D. A.; Scheidt, K. A.; Fandrick, H. W.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
76. The endo-adduct is defined as the product in which the more important substituent is on the opposite side of the epoxy bridge, whereas the ero-adduct indicates the product in which the more important substituent is on the same side as the epoxy bridge, as previously defined for exo-brevicomin.
77. Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
78. The reaction in the absence of Lewis acid proceeded with endoselectivity both at room temperature (endo:exo = 71:29) and -25 7deg;C (endo:exo = 81: 19), see ref 17d.
79. (a) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095.
80. (b) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.