Cationic bis(oxazoline) and pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7481-7484

  Evans, David A ^a   Kozlowski, Marisa C ^a   Tedrow, Jason S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID; NORBORNANE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030583498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01697-8     Document Type: Article

References (16)

1. 1) (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
2. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
3. 2) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
4. 3) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
5. 4) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508.
6. 5) Hathaway, B. J. in Comprehensive Coordination Chemistry, Wilkinson, G. Ed.; Pergamon Press, New York, N.Y.; 1987; Vol. 5, Chapter 53.
7. th ed.
8. 2 58%; R = Ph, 30%. For the details of running these reactions see ref 1 and 2.
9. 2, O.2 M in dienophile and 5 equiv of diene with 10 mol% of catalyst. Enantiomer ratios were determined by chiral HPLC using a Daicel ODH column.
10. 2, 53%; R = Ph, 92%.
11. 10) (a) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810.
12. (b) Desimoni, G.; Faita, G.; Righetti, R. P. Tetrahedron Lett. 1996, 37, 3027-3030. The bias for the phenyl substituent with metals that coordinate in a tetrahedral geometry could result from both steric and electronic effects. Possible contributions from electronic effects have not yet been addressed.
13. 11) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728-729.
14. 12) Otto, S.; Bertoncin, F.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1996, 118, 7702-7707.
15. 2, 85% ee, (S) configuration.
16. 14) The related Cu(II) and Zn(II) complexes of the tridentate ligand 2,6-diacetylpyridyl dioxime are square pyramidal and trigonal pyramidal respectively. Nicholson, G. A.; Petersen, J. L.; McCormick, B. J. Inorg. Chem. 1982, 21, 3274-3280.