Highly stereoselective addition of Grignard reagents to C- cyclopropylnitrone via the bisected s-trans conformation. An efficient synthesis of PEDC, a potent NMDA receptor antagonist having a cyclopropane structure

Tetrahedron Letters

Volumn 41, Issue 28, 2000, Pages 5373-5377

  Kazuta, Yuji ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2 (1 AMINOETHYL) N,N DIETHYL CYCLOPROPANECARBOXAMIDE; CYCLOPROPANE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; NITRONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG CONFORMATION; DRUG SYNTHESIS; EPILEPSY; ISCHEMIA; STEREOCHEMISTRY; STROKE;

EID: 0034622303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00823-6     Document Type: Article

References (23)

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6. (a) Stereoselective hydride reductions of cyclopropylcalbonyls: (a) Meyers, A. I.; Romine, J. L.; Fleming, S. A. J. Am. Chem. Soc. 1988, 110, 7245-7247. (b) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1995, 60, 2474-2487; and hydroboration of isopropenylcyclopropanes: (c) Cossy, J.; Blanchard, N.; Hamel, C.; Meyer, C. J. Org. Chem. 1999, 64, 2608-2609, which are likely to be via the bisected conformations, have also been reported.
7. (a) Stereoselective hydride reductions of cyclopropylcalbonyls: (a) Meyers, A. I.; Romine, J. L.; Fleming, S. A. J. Am. Chem. Soc. 1988, 110, 7245-7247. (b) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1995, 60, 2474-2487; and hydroboration of isopropenylcyclopropanes: (c) Cossy, J.; Blanchard, N.; Hamel, C.; Meyer, C. J. Org. Chem. 1999, 64, 2608-2609, which are likely to be via the bisected conformations, have also been reported.
8. (a) Stereoselective hydride reductions of cyclopropylcalbonyls: (a) Meyers, A. I.; Romine, J. L.; Fleming, S. A. J. Am. Chem. Soc. 1988, 110, 7245-7247. (b) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1995, 60, 2474-2487; and hydroboration of isopropenylcyclopropanes: (c) Cossy, J.; Blanchard, N.; Hamel, C.; Meyer, C. J. Org. Chem. 1999, 64, 2608-2609, which are likely to be via the bisected conformations, have also been reported.
9. (a) Shuto, S.; Ono, S.; Hase, Y.; Kamiyama, N.; Matsuda, A. Tetrahedron Lett. 1996, 37, 641-644.
10. (b) Shuto, S.; Ono, S.; Hase, Y.; Ueno, Y.; Noguchi, T.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1996, 39, 4844-4852.
11. (c) Shuto, S.; Ono, S.; Imoto, H.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1998, 41, 3507-3514.
12. (d) Noguchi, T.; Ishii, K.; Imoto, H.; Otubo, Y.; Shuto, S.; Ono, S.; Matsuda, A.; Yoshii, K. Synapus 1999, 31, 87-96.
13. 3 (Turnbull, K. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; 1995; Vol 7, pp. 4509-4512) is unsuitable for the large-scale preparation of the compounds; and (2) alkyl groups which can be introduced at the 1′-position are limited, which prevents further structure-activity relationship studies.
14. The X-ray crystallographic structure of the nitrone 2 also demonstrated that it exists in the bisected s-trans conformation in the solid state.
15. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
16. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
17. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
18. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
19. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
20. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
21. For examples, see: (a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313-1316. (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. (c) Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729. (d) Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, F. J. Org. Chem. 1997, 62, 5497-5507. (e) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1998, 63, 2371-2374. (f) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. (f) Dondoni, A.; Perrone, D. Aldrichimica Acta 1997, 30, 35-46. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
22. (f) Dondoni, A. Synthesis 1998, 1681-1706. In these reactions, the facial selectivity has been explained to be via the chelation-controlled pathway.
23. 2O.