Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline) copper(II) catalyzed hetero Diels-Alder and ene reactions. Crystallographic and mechanistic studies

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2879-2882

  Evans, David A ^a   Johnson, Jeffrey S ^a   Burgey, Christopher S ^a   Campos, Kevin R ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033537902     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00395-0     Document Type: Article

References (35)

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8. Hetero Diels-Alder: (g) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895;
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11. Ene: (j) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824.
12. See, for example: (a) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599 and references therein;
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18. The authors attributed the turnover to a change in metal geometry from square planar to tetrahedral: (a) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757;
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26. For example: (a) Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Angew. Chem. Int. Ed. Eng. 1987, 26, 1184 and references therein;
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33. Slow addition of the enol ether solved the problem of catalyst (S,S)-2a decomposition at 25 °C (ref. 1g).
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35. The possibility of a planar→tetrahedral equilibrium in solution has been probed using a number of bis(Nalkylsalicylaldiminato)copper(II) complexes; no evidence for such an equilibrium was found. See: Knoch, R.; Wilk, A.; Wannowius, K. J.; Reinen, D.; Elias, H. Inorg. Chem. 1990, 29, 3799.