Stereocontrolled synthesis of cyclopropanol amino acids from allylic sulfones: Conformationally restricted building blocks

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3687-3690

  Díez, David ^a   Garcia, P ^a   Marcos, Isidro S ^a   Garrido, N M ^a   Basabe, P ^a   Broughton, Howard B ^b   Urones, Julio G ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b ELI LILLY AND COMPANY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINO ACID; CYCLOPROPANOL; ETHER DERIVATIVE; GLUTAMIC ACID; PROPANOL; SULFONE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; CYCLOPROPANATION; ENANTIOMER; MOLECULAR DYNAMICS; MOLECULAR MODEL; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALLYL COMPOUNDS; AMINO ACIDS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; ETHERS, CYCLIC; GLUTAMIC ACID; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES;

EID: 0142011119     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035451d     Document Type: Article

References (26)

1. Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511-542.
2. Salaün, J. Top. Curr. Chem. 2000, 207, 1-67.
3. (a) Asai, A.; Mizukami, T.; Yamashita, Y.; Akinaga, S.; Ikeda, S.; Kanda, Y. Eur. Patent 1166781, 2002; Chem Abstr. 2002, 133, 120677.
4. (b) Asai, A.; Hasegawa, A.; Ochiai, K.; Yamashita, Y.; Mizukami, T. J. Antibiot. 2000, 53, 81-83
5. (a) Brandl, M.; Kozhushkov, S. I.; Loscha, K.; Kokoreva, O. V.; Yufit, D. S.; Howard, J. A. K.; de Meijere, A. Synlett 2000, 1741-1744.
6. (b) Larionov, O. V.; Savel'eva, T. F.; Kochetkov, K. A.; Ikonnokov, N. S.; Kozhushkov, S. I.; Yufit, D. S.; Howard, J. A. K.; Khrustalev, V. N.; Belokon, Y. N.; de Meijere, A. Eur. J. Org. Chem. 2003, 869-877.
7. (c) Armstrong, A.; Scutt, J. M. Org. Lett. 2003, 5, 2331-2334.
8. MacroModel v8.1.031; Schrodinger, LLC: Portland, OR.
9. (a) Diez, D.; García, P.; Pacheco, M. P.; Marcos, I. S.; Garrido, N. M.; Basabe, P. and Urones, J. G. Synlett 2002, 355.
10. (b) Diez, D.; García, P.; Marcos, I. S.; Garrido, N. M.; Basabe, P., Urones, J. G. Synthesis 2003, 53
11. Díez, D.; San Feliciano, S. G.; Marcos, I. S.; Basabe, P.; Garrido, N. M.; Urones, J. G. Synthesis 2001, 1069.
12. Piffl, M.; Weston, J.; Günther, W.; Anders, E. J. Org. Chem. 2000, 65, 5942
13. Sybyl, version 6.9; Tripos, Inc.: St. Louis, MO.
14. Spartan 02 Windows; Wavefunction, Inc.: Irvine, CA.
15. (a) Bäckvall, J.-E.; Juntunen, S. K. J. Org. Chem. 1988, 53, 2398.
16. (b) Fuchs, P. L.; Hentemann, M. F. Org. Lett. 1999, 1, 1355. Iradier, F. ; Arrayas, R. G.; Carretero, J. C. Org. Lett. 2001, 3, 2957.
17. (b) Fuchs, P. L.; Hentemann, M. F. Org. Lett. 1999, 1, 1355. Iradier, F. ; Arrayas, R. G.; Carretero, J. C. Org. Lett. 2001, 3, 2957.
18. (c) Padwa, A.; Murphree, S. S.; Ni, Z. J. J. Org. Chem. 1996, 61, 3829.
19. (f) Bäckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291
20. (e) Iradier, F.; Arrayas, R. G.; Carretero, J. C. Org. Lett. 2001, 3, 2957.
21. (f) Bäckwall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291
22. Simpkins, N. S. Sulphones in Organic Synthesis. In Tetrahedron Organic Series; Pergamon: New York, 1993.
23. Schöllkopf, U.; Pettig, D.; Busse U. Synthesis 1986, 737-740.
24. (a) Williams, R. M. Synthesis of Optically Active α-Amino Acids. In Tetrahedron Organic Series; Pergamon: New York, 1989.
25. (b) Schöllkopf, U.; Kühnle, W; Egert, E.; Dyrbusxch, M. Angew. Chem., Int. Ed. 1987, 26, 480-482.
26. (c) Ojea, V.; Conde, S.; Ruiz, M.; Fernández, M. C.; Quintela, J. M. Tetrahedron Lett. 1997, 38, 4311-4314.