Enhanced reactivity of tuned imidazolidin-2-one chiral auxiliaries in Diels-Alder reactions

Tetrahedron Asymmetry

Volumn 9, Issue 6, 1998, Pages 923-926

  Roos, Gregory H P ^a   Balasubramaniam, Sundari ^b  

^a SULTAN QABOOS UNIVERSITY   (Oman)

^b MURDOCH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHIRALITY; CRYSTALLIZATION; PRIORITY JOURNAL; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0032571512     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00070-6     Document Type: Article

References (16)

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2. for sample reviews, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series Volume 8, Pergamon Press, Oxford, 1990; (b) Oppolzer, W. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Paquette, L. A., Eds., Pergamon Press, Oxford, 1991.
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5. (c) Lautens, M., Klute, W., Tam, W. Chem. Rev., 1996, 96, 49-92 and references therein.
6. Jensen, K. N., Roos, G. H. P. Tetrahedron: Asymmetry, 1992, 3, 1553-1554.
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9. Evans, D. A., Chapman, K. T., Bisaha, J. J. Am. Chem. Soc., 1988, 110, 1238-1256.
10. For sample applications, see: (a) Doyle, M. P., Dyatkin, A. B., Roos, G. H. P., Cãnas, F., Pierson, D., van Basten, A., Müller, P., Polleux, P. J. Am. Chem. Soc., 1994, 116, 4507; (b) Doyle, M. P., Zhou, Q.-L., Raab, C. E., Roos, G. H. P. Tetrahedron Lett., 1995, 36, 4745-4748.
11. For sample applications, see: (a) Doyle, M. P., Dyatkin, A. B., Roos, G. H. P., Cãnas, F., Pierson, D., van Basten, A., Müller, P., Polleux, P. J. Am. Chem. Soc., 1994, 116, 4507; (b) Doyle, M. P., Zhou, Q.-L., Raab, C. E., Roos, G. H. P. Tetrahedron Lett., 1995, 36, 4745-4748.
12. Roos, G. H. P., Doyle, M. P., Balasubramaniam, S., Raab, C. E. Synth. Commun., 1996, 26, 2165-2175.
13. All new compounds gave satisfactory analytical and spectral data consistent with the structures shown.
14. 2:EtOAc:hexane eluant (1:5:94). Retention times: endo II 9.1; exo I 9.6; exo II 10.0; endo I 10.7 min.
15. Initial results of this work were presented at the Royal Australian Chemical Institute Organic Chemical Congress, Rockhampton, July 1996.
16. 2:EtOAc:hexane eluant (1:5:94). Retention times of isoprene adduct: major 18.4; minor 19.1 min. Piperylene adduct: major 13.6; minor 12.3 min.