(S)-Ethyl 4,4-dimethyl pyroglutamate as a new 'quat' chiral auxiliary in aldol condensations

Tetrahedron Asymmetry

Volumn 8, Issue 5, 1997, Pages 669-671

  Ezquerra, Jesús ^a   Rubio, Almudena ^a   Martín, Justina ^b   Navío, José Luis García ^b  

^a CSIC   (Spain)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 2 METHYLPROPIONIC ACID; 4,4 DIMETHYLPYROGLUTAMIC ACID ETHYL ESTER; PROPIONIC ACID DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031053485     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00028-1     Document Type: Article

References (12)

1. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach. Pergamon Press: New York, 1983, Chapter 2.
2. For a review see: Heatcock, C. H. Aldrichimica 1990, 23, 99-111.
3. Sibi, M. P.; Deshpande, P. K.; Ji, J. Tetrahedron Lett. 1995, 36, 8965-8967.
4. (a) Tomioka, K.; Suenaga, T.; Koga, K. Tetrahedron Lett. 1986, 27, 369-372.
5. (b) Kanai, M.; Muraoka, A.; Tanaka, T.; Sawada, T.; Ikota, N.; Tomioka, K. Tetrahedron Lett. 1995, 36, 9349-9352.
6. Davies, S. G.; Doisneau, G. J.-M.; Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2369-2372.
7. Ethyl pyroglutamate was prepared as described by: Silverman, R. B.; Levy, M. A. J. Org. Chem. 1980, 45, 815-818.
8. (b) The N-urethane protection was made as described by: Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426
9. Ezquerra, J.; Pedregal, C.; Rubio, A.; Vaquera, J. J.; Matía, M. P.; Martín, J.; Diaz, A.; García Navío, J. L. J. Org. Chem. 1994, 59, 4327-4331.
10. Davies, S. G.; Doisneau, G. J.-M.; Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2373-2376.
11. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
12. 7).