Stereoselective synthesis of α,α′-biprolines

Organic Letters

Volumn 7, Issue 1, 2005, Pages 35-38

  Vartak, Ashish P ^a   Young Jr , Victor G ^b   Johnson, Rodney L ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; HALIDE; OXAZOLIDINONE DERIVATIVE; PROLINE DERIVATIVE; DIPEPTIDE; PROLINE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DIMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; DIPEPTIDES; MODELS, MOLECULAR; PROLINE; STEREOISOMERISM;

EID: 12344265215     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047958+     Document Type: Article

References (18)

1. Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561.
2. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
3. (a) Blaser, D.; Seebach, D. Lieb. Ann. Chem. 1991, 10, 1067-1078.
4. (b) Seebach, D.; Mueller, S. G.; Gysel, U.; Zimmermann, J. Helv. Chim. Acta 1988, 71, 1303-1318.
5. (c) Smith, A. B., III; Pasternak, A.; Yokoyama, A.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 8977-8980.
6. (a) Beck, A. K.; Blank, S.; Job, K.; Seebach, D.; Sommerfeld, T. Org. Synth. 1995, 72, 62-73.
7. (b) Isono, N.; Mori, M. J. Org. Chem. 1996, 61, 7867-7862.
8. 4). No molecular structure with similar attributes was found in the Cambridge Structural Database (Allen, F. H. Acta Crystallogr. 2002, B58, 380-388).
9. Alvarez-Ibarra, C.; Csaky, A. G.; Colemenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482.
10. Chen, Y.; Yudin, A. K. Tetrahedron Lett. 2003, 44, 4865-4868.
11. Goetze, J.; Kampfer, H. Chem. Ber. 1966, 99, 1851-1860.
12. Saleur, D.; Bouillon, J. P.; Portella, C. Tetrahedron Lett. 2000, 41, 321-324.
13. Obata, N.; Niimura, K. J. Chem. Soc., Chem. Commun. 1977, 238-239.
14. Pradhan, B. P.; Chakraborty, S.; Sinha, R. P. Ind. J. Chem. 1995, 34B, 178-182.
15. Mayr, H.; Armin, R. O.; Ernst-Ulrich, W.; Nicola, C. A. J. Am. Chem. Soc. 1997, 119, 12727-12733.
16. Grob, C. A. Angew. Chem., Int. Ed. Engl. 1969, 8, 535-546.
17. Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4767-4968.
18. 1H NMR of 14 at 4.37 ppm indicated that it was the oxazolidinone ring with the Cα(S) configuration of 4 that had been hydrolyzed.