The first enantioselective synthesis of both Diels-Alder enantiomers with the same bis(oxazoline)-magnesium perchlorate chiral catalyst

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3027-3030

  Desimoni, Giovanni ^a   Faita, Giuseppe ^a   Righetti, Pier Paolo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029881335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00460-1     Document Type: Article

References (16)

1. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
2. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807.
3. Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
4. Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 798.
5. For an excellent review see: Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
6. Narasaka, K.; Inoue, M.; Yamada, T. Chemistry Letters 1986, 1967.
7. Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757.
8. Castellino, S.; Dwight, W. J. J. Am. Chem. Soc. 1993, 115, 2986.
9. For the effect of inorganic perchlorates on the DA reaction see e.g. (a) Grieco, P. A.; Nunes, J.J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595;
10. (b) Casaschi, A.; Desimoni, G.; Faita, G.; Invernizzi Gamba, A.; Lanati, S.; Righetti, P. P. J. Am. Chem. Soc. 1993, 115, 8002 and references therein.
11. Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron Lett. 1995, 36, 2855.
12. 23 value was determined on this sample, without any further purification.
13. 3].
14. 2O that gave (S)-3 with 24% e.e..
15. For the importance of the octahedral coordination of magnesium ion see: Black, C.B.; Huang, H.-W.; Cowan, J.A. Coord. Chem. Rev. 1994, 135/136, 165.
16. If the water molecules are in the equatorial and axial sites, again the Si-face becomes the sterically more accessible as reported by Corey in ref. 1. Structures 6 and 7 are Hyperchem-Chemplus representations.