Urea-catalyzed transthioesterification: Towards a new kinetic resolution methodology

Arkivoc

Volumn 2011, Issue 4, 2011, Pages 115-126

  Tallon, Seán ^a   Lawlor, Alana C ^a   Connon, Stephen J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Hydrogen bonding; Organocatalysis; Thioester; Transthioesterification; Urea

Indexed keywords

EID: 79955416076     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.410     Document Type: Article

References (34)

1. Wieland, T. Angew. Chem. 1954, 66, 507.
2. (a) Sheehan J. C., Beck C W. J. Am. Chem. Soc. 1955, 77, 4875.
3. (b) Sachs H., Waelsch H. J. Am. Chem. Soc. 1955, 77, 6601.
4. th ed.); W. H. Freeman and Company: New York, 2002, p 621.
5. (a) Dawson, P. E.; Muir, T.W.; Clark-Lewis, I; Kent, S. B. Science 1994, 266, 776.
6. (b) Wieland, T.; Bokelman, E.; Bauer, L.; Lang, H. U.; Lau, H. Justus Liebigs Ann. Chem. 1953, 583, 129.
7. (a) Dawson P. E., Kent S. B. H. Annu. Rev. Biochem. 2000, 69, 923.
8. (b) Macmillan D. Angew. Chem. Int. Ed 2006, 45, 7668.
9. Johnson, E. C B.; Kent, S. B. H. J. Am. Chem. Soc 2006, 128, 6640
10. For an example of the use of activated thiophenol-derived thioester intermediates to accelerate an otherwise slow process see: Cronin, L.; Manoni, F.; O' Connor, C J.; Connon, S. J. Angew. Chem. Int. Ed 2010, 49, 3045.
11. Peschiulli, A.; Procuranti, B.; O' Connor, C J.; Connon, S. J. Nature Chemistry, 2010, 2, 380.
12. (a) Maher D. J., Connon S. J., Tetrahedron Lett. 2004, 45, 1301.
13. (b) Procuranti B., Connon S. J., Chem. Commun. 2007, 1421.
14. (c) Peschiulli, A.; Gun'ko, Y.; Connon, S. J. J. Org Chem. 2008, 73, 2454.
15. (d) Peschiulli, A; Quigley, C.; Tallon, S.; Gun'ko, Y. K.; Connon, S. J. J. Org Chem. 2008, 73, 6409.
16. (a) McCooey S. H., Connon S. J. Angew. Chem. Int. Ed 2005, 44, 6367.
17. (b) McCooey S. H.; McCabe, T.; Connon, S. J. J. Org Chem. 2006, 71, 7494.
18. (c) Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037.
19. (a) Fleming, E. M.; Quigley, C.; Rozas, I; Connon, S. J. J. Org Chem. 2008, 73, 948.
20. (b) Kavanagh, S. A.; Piccinini, A.; Fleming, E M.; Connon, S. J. Org Biomol. Chem. 2008, 6, 1339.
21. Sturdik, E.; Antalik, M.; Sulo, P.; Balaz, S.; Durcova, E.; Drobnica, L. Coll. Czech. Chem. Commun. 1985, 50, 2065
22. a values (25 °C) are taken from: (a) (DABCO) Hine, J.; Kaufmann, C.; Cholod, S. J. Am. Chem. Soc. 1987, 52, 2091.
23. (b) (DMAP) Chrystuik, E.; Williams, A. J. Am. Chem. Soc 1987, 109, 3040.
24. (c) (DIPEA) Fujii, T.; Nishida, H.; Abiru, Y.; Yamamoto, M.; Kise, M. Chem. Pharm. Bull. 1995, 43, 1872.
25. (d) (NMI) Appleton D. W.; Sarkar, B. Proc. Nat Acad Sci. USA 1974, 71, 1686.
26. (e) (NEM) Metzler, D. E.; Metzler, C M. Biochemistry: The Chemical Reactions of Living Cells, Vol. 2, Academic Press, 2001, pp 99-100.
27. Since DABCO-Bz possesses a different counteranion to that associated with the putative intermediate in the DABCO-catalyzed process it is perhaps not surprising that the chemical shifts are marginally different. We could show that the putative intermediate is not the conjugate acid of DABCO by comparing the spectrum shown in Figure 1B with that obtained following addition of one equivalent of TFA to DABCO in dichloromethane.
28. a of DMAP is much more closely matched to that of the attacking nucleophile, so a general base-catalyzed process may predominate
29. It seems likely that the decomposition of 11 under these conditions is problematic
30. It is noteworthy that the ideal yield for this process from a kinetic resolution perspective is 50%)
31. A separate experiment using 5 mol% catalyst loading conversion reached only 12% conversion after 44 h.
32. Peschiulli, A. Ph.D. Thesis, The University of Dublin, 2010.
33. Launay, J. P.; Tourell-Paygis, M.; Lipster, J. F.; Marvaud, V.; Joachin, C Inorg. Chem. 1991, 30, 1033.
34. Chakraborti, A. K.; Shivani. J. Org. Chem. 2006, 71, 5785.