Studies toward Lewis basic thiocarbamate and thiourea mediated bromolactonization: The effect of a trace amount of water on the reactivity and enantioselectivity

Tetrahedron Letters

Volumn 52, Issue 38, 2011, Pages 4892-4895

  Tan, Chong Kiat ^a   Chen, Feng ^a   Yeung, Ying Yeung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Asymmetric reaction; Bromolactonization; Catalysis; Lewis base; Water effect

Indexed keywords

THIOCARBAMIC ACID; THIOUREA; WATER;

ARTICLE; BROMOLACTONIZATION; CATALYSIS; ENANTIOSELECTIVITY; LACTONIZATION; MOISTURE; REACTION TIME; WATER CONTENT;

EID: 84860390566     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.07.049     Document Type: Article

References (36)

1. F. Rodríguez, and F.J. Fañanás S. Ma, Handbook of Cyclization Reactions Vol. 4 2010 Wiley-VCH New York 951 990
2. S. Hajra, S. Bar, D. Sinha, and B. Maji J. Org. Chem. 73 2008 4320 4332
3. S.E. Denmark, and M.T. Burk Proc. Natl. Acad. Sci. 107 2010 20655 20660
4. P.A. Bentley, Y. Mei, and J. Du Tetrahedron Lett. 49 2008 1425 1427
5. S.M. Ahmad, D.C. Braddock, G. Cansell, S.A. Hermitage, J.M. Redmond, and A.J.P. White Tetrahedron Lett. 48 2007 5948 5952
6. D.C. Braddock, G. Cansell, S.A. Hermitage, and A.J.P. White Chem. Commun. 2006 1442 1444
7. S.A. Snyder, and D.S. Treitler Angew. Chem., Int. Ed. 48 2009 7899 7903
8. S.A. Snyder, D.S. Treitler, and A.P. Brucks J. Am. Chem. Soc. 132 2010 14303 14314
9. For examples of catalytic asymmetric halolactonizations, see: J. Haas, S. Piguel, and T. Wirth Org. Lett. 4 2002 297 300
10. M. Wang, L.X. Gao, W.P. Mai, A.X. Xia, F. Wang, and S.B. Zhang J. Org. Chem. 69 2004 2874 2876
11. J. Haas, S. Bissmire, and T. Wirth Chem. Eur. J. 11 2005 5777 5785
12. J.M. Garnier, S. Robin, and G. Rousseau Eur. J. Org. Chem. 2007 3281 3291
13. Z. Ning, R. Jin, J. Ding, and L. Gao Synlett 2009 2291 2294
14. W. Zhang, S. Zheng, N. Liu, J.B. Werness, I.A. Guzei, and W. Tang J. Am. Chem. Soc. 132 2010 3664 3665
15. D.C. Whitehead, R. Yousefi, A. Jaganathan, and B. Borhan J. Am. Chem. Soc. 132 2010 3298 3300
16. G.E. Veitch, and E.N. Jacobsen Angew. Chem., Int. Ed. 49 2010 7332 7335
17. K. Nurai, T. Matsushita, A. Nakamura, S. Fukushima, M. Shimura, and H. Fujioka Angew. Chem., Int. Ed. 49 2010 9174 9177
18. U. Hennecke, C.H. Müller, and R. Fröhlich Org. Lett. 13 2011 860 863
19. C.K. Tan, L. Zhou, and Y.-Y. Yeung Synlett 2011 1335 1339
20. For examples of catalytic asymmetric halocyclizations and related reactions, see: S.H. Kang, S.B. Lee, and C.M. Park J. Am. Chem. Soc. 125 2003 15748 15749
21. A. Sakakura, A. Ukai, and K. Ishihara Nature 445 2007 900 903
22. A. Jaganathan, A. Garzan, D.C. Whitehead, R.J. Staples, and B. Borhan Angew. Chem., Int. Ed. 50 2011 2593 2596
23. Y. Cai, X. Liu, Y. Hui, J. Jiang, W. Wang, W. Chen, L. Lin, and X. Feng Angew. Chem., Int. Ed. 49 2010 6160 6164
24. Y. Cai, X. Liu, J. Jiang, W. Chen, L. Lin, and X. Feng J. Am. Chem. Soc. 133 2011 5636 5639
25. G. Chen, and S. Ma Angew. Chem., Int. Ed. 49 2010 8306 8308
26. A. Castellanos, and S.P. Fletcher Chem. Eur. J. 17 2011 5766 5776
27. L. Zhou, J. Chen, C.K. Tan, and Y.-Y. Yeung J. Am. Chem. Soc. 133 2011 9164 9167
28. For studies on the challenges of halolactonization, see: R.S. Brown Acc. Chem. Res. 30 1997 131 137
29. X.-L. Cui, and R.S. Brown J. Org. Chem. 65 2000 5653 5658
30. S.E. Denmark, M.T. Burk, and A.J. Hoover J. Am. Chem. Soc. 132 2010 1232 1233
31. L. Zhou, C.K. Tan, X. Jiang, F. Chen, and Y.-Y. Yeung J. Am. Chem. Soc. 132 2010 15474 15476
32. C.K. Tan, and L. Zhou Org. Lett. 13 2011 2738 2741
33. For a related study using a Lewis basic sulfur to activate a phenylselenium reagent in selenolactonization, see: S.E. Denmark, and W.R. Collins Org. Lett. 9 2007 3801 3804
34. P.D. Boyle, and S.M. Godfrey Coord. Chem. Rev. 223 2001 265 299
35. A.J. Arduengo, and E.M. Burgess J. Am. Chem. Soc. 99 1977 2376 2378
36. For one of the possible water decomposition pathways, see: R.D. Tiwari, and U.C. Pande Analyst 1969 813 814