Enantioselective Diels-Alder reactions: Novel constrained bis(oxazoline) ligand-metal triflate catalysts

Tetrahedron Asymmetry

Volumn 8, Issue 18, 1997, Pages 3079-3087

  Takacs, James M ^a   Quincy, David A ^a   Shay, William ^a   Jones, Brian E ^a   Ross II, Charles R ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030984060     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00323-6     Document Type: Article

References (19)

1. Takacs, J. M.; Lawson, E. C.; Reno, M. J.; Youngman, M. A.; Quincy, D. A. Tetrahedron: Asymmetry 1997, 8, 3073-78.
2. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-10.
3. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-1.
4. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173-80.
5. The crystal structure of the bicyclo[2.2.2]-1,4-box ligand 7a as determined by X-ray methods is shown below in stereoview. The dihedral angle defined by C(2) of the two oxazoline moieties is 113°. (matrix presented)
6. Davies, I. W.; Gerena, L.; Castonguay, L.; Sennayake, C. H.; Larson, R. D.; Verhoeven, T. R.; Reider, P. J. Chem. Commun. 1996, 1753-4.
7. Harm, A. M.; Knight, J. G.; Stemp, G. Synlett 1996, 677-8.
8. Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 4073-6.
9. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 2453-6.
10. Furuta, K.; Iwanaga, K.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 4507-4510.
11. Heathcock, C. H.; Davis, B. R.; Hadley, C. R. J. Med. Chem. 1989, 32, 197.
12. The bis(hydroxyamide) intermediates synthesized in the course of this study often proved difficult to handle due to poor solubility and/or the tendency to form gels in common organic solvents.
13. Denmark, S. E.; Makajima, N.; Nicase, O. J.-C.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884-92; and references cited therein.
14. Vorbruggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471-4.
15. Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757-62.
16. See also: Davies, I. W.; Gerena, L.; Cai, D.; Larson, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145-8.
17. Scharf, H.-D.; VaBen, R.; Runsink, J. Chem. Ber. 1986, 119, 3492-7.
18. Matsuda, H.; Kanai, H. J. Mol. Catal. 1985, 29, 157-64.
19. Jacques, J.; Brienne, M.-J. Bull. Soc. Chim. Fr. 1973, 190-7.