Diastereoselective Reaction of Buta-1,3-diene with Chiral Derivatives of Glyoxylic Acid: Effective Route to Optically Pure 2-Substituted 3,6-Dihydro2H-pyrans

Synthesis

Volumn , Issue 1, 2004, Pages 87-91

  Kosior, Magorzata ^a   Asztemborska, Monika ^b   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Catalysis; Chiral auxiliaries; Diels Alder reactions; Lewis acids; Stereoselectivity

Indexed keywords

CARBOXYLIC ACIDS; DERIVATIVES; NITROGEN COMPOUNDS;

DIASTEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

8 PHENYLMENTHYLGLYOXYLATE; ALKENE DERIVATIVE; BUTA 1,3 DIENE; GLYOXYLIC ACID DERIVATIVE; LEWIS ACID; N GLYOXYLOYLBORNANE 10,2 SULTAM; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; GAS CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TECHNIQUE;

EID: 0347319073     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44372     Document Type: Article

References (13)

1. Jirousek, M. R.; Gilling, J. R.; Gonzalez, C. M.; Heath, W. F.; McDonald, J. H. III; Neel, D. A.; Rito, C. J.; Singh, U.; Stramm, L. E.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L. M.; Hall, S. E.; Winneroski, L. L.; Faul, M. M. J. Med. Chem. 1996, 39, 2664.
2. Jirousek, M. R.; Gilling, J. R.; Neel, D. A.; Rito, C. J.; O'Bannon, D.; Heath, W. F.; McDonald, J. H. III; Faul, M. M.; Winneroski, L. L.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L. M.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2093.
3. Engel, G. L.; Farid, N. A.; Faul, M. M.; Richardson, L. A.; Winneroski, L. L. Int. J. Pharm. 2000, 198, 239.
4. Faul, M. M.; Winneroski, L. L.; Krumrich, C. A.; Sullivan, K. A.; Gilling, J. R.; Neel, D. A.; Rito, Ch. J.; Jirousek, M. R. J. Org. Chem. 1998, 63, 1961.
5. Cossy, J.; Bouzbouz, S.; Caille, J.-C. Tetrahedron: Asymmetry 1999, 10, 3859.
6. Faul, M. M.; Krumrich, C. A. J. Org. Chem. 2001, 66, 2024.
7. Kosior, M.; Malinowska, M.; Jóźwik, J.; Caille, J.-C.; Jurczak, J. Tetrahedron: Asymmetry 2003, 14, 239.
8. Kwiatkowski P., Kosior M., Asztemborska M., Jurczak J.; unpublished results
9. (a) Oppolzer, W.; Chapuis, C.; Bernardinelli, G. Helv. Chim. Acta 1984, 67, 1397.
10. (b) Bauer, T.; Jeżwski, A.; Chapuis, C.; Jurczak. J. Tetrahedron: Asymmetry 1996, 7, 1385.
11. (a) Fernandez, F.; Garcia, G.; Rodriguez, J. E. Synth. Commun. 1990, 20, 2837. (b) Freund, R.; Mahboobi, S.; Noack, K.; Schönholzer, P.; Bernauer, K. Helv. Chim. Acta 1990, 73, 439. (c) Freund, R.; Martinovic, S.; Bernauer, K. Helv. Chim. Acta 1992, 75, 282.
12. (a) Fernandez, F.; Garcia, G.; Rodriguez, J. E. Synth. Commun. 1990, 20, 2837. (b) Freund, R.; Mahboobi, S.; Noack, K.; Schönholzer, P.; Bernauer, K. Helv. Chim. Acta 1990, 73, 439. (c) Freund, R.; Martinovic, S.; Bernauer, K. Helv. Chim. Acta 1992, 75, 282.
13. (a) Fernandez, F.; Garcia, G.; Rodriguez, J. E. Synth. Commun. 1990, 20, 2837. (b) Freund, R.; Mahboobi, S.; Noack, K.; Schönholzer, P.; Bernauer, K. Helv. Chim. Acta 1990, 73, 439. (c) Freund, R.; Martinovic, S.; Bernauer, K. Helv. Chim. Acta 1992, 75, 282.