Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

Tetrahedron Asymmetry

Volumn 19, Issue 11, 2008, Pages 1356-1362

  Abraham, Elin ^a   Davies, Stephen G ^a   Docherty, Alexander J ^a   Ling, Kenneth B ^a   Roberts, Paul M ^a   Russell, Angela J ^a   Thomson, James E ^a   Toms, Steven M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 5 TRIS(PHENYLTHIO)METHYLCYCLOPENTANE; 2 AMINOCYCLOPENTANECARBOXYLIC ACID; 5 METHYLCISPENTACIN; AMIDE; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; ESTER; LITHIUM DERIVATIVE; LITHIUM N 3,4 DIMETHOXYBENZYL N (ALPHA METHYLBENZYL)AMIDE; LITHIUM N BENZYL N (ALPHA METHYLBENZYL)AMIDE; METHYL 5 TRIS(PHENYLTHIO)METHYLCYCLOPENT 1 ENE CARBOXYLATE; NICKEL;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; DEBENZYLATION; DEPROTECTION REACTION; DESULFURIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 47049123681     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.05.016     Document Type: Article

References (38)

1. For a review see:. Fülöp F. Chem. Rev. (2001) 2181
2. For example see:. Aggarwal V.K., Roseblade S.J., Barrell J.K., and Alexander R. Org. Lett. 4 (2002) 1227
3. Bohm C., Schiffers I., Atodiresi I., and Hackenberger C.P.R. Tetrahedron: Asymmetry 14 (2003) 3455
4. Aggarwal V.K., Roseblade S.J., and Alexander R. Org. Biomol. Chem. 1 (2003) 684
5. Gellman and co-workers have shown that β-peptides derived from transpentacin adopt a helical structure in the solid state and solution; see:. Dado G.P., and Gellman S.H. J. Am. Chem. Soc. 116 (1994) 1054
6. Appella D.H., Christianson L.A., Klein D.A., Powell D.R., Huang X., Barchi J.J., and Gellman S.H. Nature 387 (1997) 381
7. Fülöp and co-workers have shown that β-peptides derived from cispentacin form a sheetlike secondary structure in solution; see:. Martinek T.A., Táth G.K., Vass E., Hollósi M., and Fülöp F. Angew. Chem., Int. Ed. 41 (2002) 1718
8. Babler J.H., and Sarussi S.J. J. Org. Chem. 52 (1987) 3462
9. For kinetic resolution of 3-alkyl-cyclopent-1-ene-carboxylates see:. Bailey S., Davies S.G., Smith A.D., and Withey J.M. Chem. Commun. (2002) 2910
10. Bunnage M.E., Chippindale A.M., Davies S.G., Parkin R.M., Smith A.D., and Withey J.M. Org. Biomol. Chem. 1 (2003) 3698
11. Bunnage M.E., Davies S.G., Parkin R.M., Roberts P.M., Smith A.D., and Withey J.M. Org. Biomol. Chem. 2 (2004) 3337
12. For parallel kinetic resolution of 3-alkyl-cyclopent-1-ene-carboxylates see:. Davies S.G., Garner A.C., Long M.J.C., Smith A.D., Sweet M.J., and Withey J.M. Org. Biomol. Chem. 2 (2004) 3355
13. For kinetic and parallel kinetic resolution of 5-alkyl-cyclopent-1-ene-carboxylates see:. Davies S.G., Díez D., El Hammouni M.M., Garner A.C., Garrido N.M., Long M.J.C., Morrison R.M., Smith A.D., Sweet M.J., and Withey J.M. Chem. Commun. (2003) 2410
14. Davies S.G., Garner A.C., Long M.J.C., Morrison R.M., Roberts P.M., Savory E.D., Smith A.D., Sweet M.J., and Withey J.M. Org. Biomol. Chem. 3 (2005) 2762
15. For parallel kinetic resolution of 3-oxy-substituted cyclopent-1-ene-carboxylates see:. Aye Y., Davies S.G., Garner A.C., Roberts P.M., Smith A.D., and Thomson J.E. Org. Biomol. Chem. (2008) 10.1039/b802428f
16. Horeau A. Tetrahedron 31 (1975) 1307
17. For examples see:. Takahata H., Uchida Y., and Momose T. J. Org. Chem. 60 (1995) 5628
18. Fernandez F., Otero J.M., Estevez J.C., and Estevez R.J. Tetrahedron: Asymmetry 17 (2006) 3063
19. Perreault S., and Spino C. Org. Lett. 8 (2006) 4385
20. Shingate B.B., Hazra B.G., Pore V.S., Gonnade R.G., and Bhadbhada M.M. Tetrahedron 63 (2007) 5622
21. Manas A.-R.B., and Smith R.A.J. J. Chem. Soc., Chem. Commun. (1975) 216
22. See also:. Stork G., and Rychnovsky S.D. J. Am. Chem. Soc. 109 (1987) 1564
23. For examples see:. Braun M., Laicher F., and Meier T. Angew. Chem., Int. Ed. 39 (2000) 3494
24. Smith III A.B., Pitram S.M., Boldi A.M., Gaunt M.J., Sfouggatakis C., and Moser W.H. J. Am. Chem. Soc. 125 (2003) 14435
25. Amat M., Perez M., Llor N., Escolano C., Luque F.J., Molins E., and Bosch J. J. Org. Chem. 69 (2004) 8681
26. Shiina J., and Nishiyama S. Tetrahedron Lett. 46 (2005) 7683
27. Dambrin V., Villiéras M., Moreau C., Amri H., Toupet L., and Villiéras J. Tetrahedron Lett. 37 (1996) 6323
28. Dambrin V., Villiéras M., Janvier P., Toupet L., Amri H., Lebreton J., and Villiéras J. Tetrahedron 57 (2001) 2155
29. Le Diguarher T., Chollet A.-M., Bertrand M., Hennig P., Raimbaud E., Sabatini M., Guilbaud N., Pierre A., Tucker G.C., and Casara P. J. Med. Chem. 46 (2003) 3840
30. Ager D.J., and East M.B. J. Org. Chem. 51 (1986) 3983
31. Kar A., and Argade N.P. Tetrahedron 59 (2003) 2991
32. Cailleau T., Cooke J.W.B., Davies S.G., Ling K.B., Naylor A., Nicholson R.L., Price P.D., Roberts P.M., Russell A.J., Smith A.D., and Thomson J.E. Org. Biomol. Chem. 5 (2007) 3922
33. The high stereocontrol exerted upon protonation of an enolate anti to an adjacent heteroatom is well documented; see:. Mohrig J.R., Rosenberg R.E., Apostol J.W., Bastienaansen M., Evans J.W., Franklin S.J., Frisbie C.D., Fu S.S., Hamm M.L., Hirose C.B., Hunstad D.A., James T.L., King R.W., Larson C.J., Latham H.A., Owen D.A., Stein K.A., and Warnet R. J. Am. Chem. Soc. 119 (1997) 479
34. Banfi L., and Guanti G. Tetrahedron: Asymmetry 10 (1999) 439
35. Davies H.M.L., Hodges L.M., and Gregg T.M. J. Org. Chem. 66 (2001) 7898
36. 19F NMR spectroscopy; see. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543
37. Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518
38. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, C. K.; Watkin, D. J. crystals, Issue 11, Chemical Crystallography Laboratory, University of Oxford: UK, 2001.