Enantioselective Diels-Alder reactions: Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

Tetrahedron Asymmetry

Volumn 8, Issue 18, 1997, Pages 3073-3078

  Takacs, James M ^a   Lawson, Edward C ^a   Reno, Michael J ^a   Youngman, Mark A ^a   Quincy, David A ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; ENVIRONMENTAL TEMPERATURE; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030884898     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00322-4     Document Type: Article

References (22)

1. Takacs, J. M.; John J. Weidner; Newsome, P. W.; Takacs, B. E.; Chidambaram, R.; Shoemaker, R. J. Org. Chem. 1995, 60, 3473-86.
2. Takacs, J. M.; Lawson, E. C. Organometallics 1994, 13, 4787-93.
3. Takacs, J. M.; Chandramouli, S. V. Tetrahedron Lett. 1994, 35, 9165-8.
4. Takacs, J. M.; Quincy, D. A. in 205th ACS National Meeting Abstracts, Denver, CO, 1993, ORGN 265.
5. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-4.
6. Evans, D. A.; Murry, J. A.; Matt, P. V.; Norcross, R. D.; Miller, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800.
7. Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-30.
8. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-1.
9. Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725-6.
10. Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Chem. Commun. 1996, 1753-4.
11. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815-8.
12. Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron Lett. 1996, 37, 3027-30.
13. Desimoni, G.; Faita, G.; Invernizzi, A. G.; Righetti, P. P. Tetrahedron 1997, 53, 7671-88.
14. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-10.
15. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 729-30.
16. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
17. 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.
18. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173-80.
19. 2 complexes in the presence and absence of N-acyloxazolidinone 1, suggest that a mixture of interconverting of metal complexes is present under the conditions employed for Table 1.
20. Davies, I. W.; Gerena, L.; Cai, D.; Larson, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1997, 38, 1145-8.
21. 2]. The crystal structure of this tetrahedral zinc complex is shown below in stereoview. The dihedral angle defined by C(2) of the two oxazoline moieties is approximately 72°. (matrix presented)
22. Sibi, M. P.; Ji, J.; Gürtler, J. H. S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-1.