Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Chemical Communications

Volumn 47, Issue 12, 2011, Pages 3395-3397

  MacLellan, Paul ^a   Clayden, Jonathan ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLTHIOL DERIVATIVE; TERTIARY THIOL DERIVATIVE; THIOCARBAMIC ACID; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DEPROTECTION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; LITHIATION; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79952369434     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c0cc04912c     Document Type: Article

References (40)

1. M. Shibasaki, M. Kanai, Chem. Rev., 2008, 108, 2853
2. O. Riant, J. Hannedouche, Org. Biomol. Chem., 2007, 5, 873
3. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem., 2007, 5969
4. F. Schmidt, R. T. Stemmler, J. Rudolph, C. Bolm, Chem. Soc. Rev., 2006, 35, 454
5. E. J. Corey, A. Guzman-Perez, Angew. Chem., Int. Ed., 1998, 37, 388
6. M. Hatano, K. Ishihara, Synthesis, 2008, 1647
7. P. I. Dosa, G. C. Fu, J. Am. Chem. Soc., 1998, 120, 445
8. A. Ohno, K. Nakamura, Y. Shizume, S. Oka, Bull. Chem. Soc. Jpn., 1977, 50, 1003
9. P. Metzner, J. Vialle, A. Vibet, Tetrahedron Lett., 1976, 4295
10. J. Voss, J. Sulfur Chem., 2009, 30, 167
11. J. Clayden, et al., Organic Chemistry, OUP, Oxford, 2001, p. 4
12. G. W. Kutney, K. Turnbull, J. Chem. Educ., 1984, 61, 372
13. Y. Mukaiyama, K. Ikegai, W. Pluempanupat, Chem. Lett., 2005, 34, 638
14. Y. Mukaiyama, K. Ikegai, W. Pluempanupat, Bull. Chem. Soc. Jpn., 2006, 79, 780
15. M. Kellogg, B. Strijtveen, Tetrahedron, 1987, 43, 5039
16. J. M. McFadden, G. L. Frehywot, C. A. Townsend, Org. Lett., 2002, 4, 3859
17. C. Palomo, M. Oiarbide, F. Dias, R. Lopez, A. Linden, Angew. Chem., Int. Ed., 2004, 43, 3307
18. C. Palomo, M. Oiarbide, F. Dias, R. T. Lopez, P. B. Gonzalez, E. Gomez-Bengoa, J. M. Saa, A. Linden, J. Am. Chem. Soc., 2006, 128, 15236
19. J. Clayden, W. Farnaby, D. M. Grainger, U. Hennecke, M. Mancinelli, D. J. Tetlow, I. H. Hillier, M. A. Vincent, J. Am. Chem. Soc., 2009, 131, 3410
20. A. M. Fournier, R. A. Brown, W. Farnaby, H. Miyatake-Ondozabal, J. Clayden, Org. Lett., 2010, 12, 2222
21. J. Clayden, F. E. Knowles, C. J. Menet, Tetrahedron Lett., 2003, 44, 3397
22. J. Clayden, S. Parris, N. Cabedo, A. H. Payne, Angew. Chem., Int. Ed., 2008, 47, 5060
23. O. Stratmann, B. Kaiser, R. Fröhlich, O. Meyer, D. Hoppe, Chem.-Eur. J., 2001, 7, 423
24. F. Marr, D. Hoppe, Org. Lett., 2002, 4, 4217
25. F. Marr, R. Fröhlich, D. Hoppe, Org. Lett., 1999, 1, 2081
26. H. E. Zimmerman, L. Singer, B. S. Thyagarajan, J. Am. Chem. Soc., 1959, 81, 108
27. E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994
28. Y. Kawano, N. Kaneko, T. Mukaiyama, Chem. Lett., 2005, 34, 1612
29. R. A. Batey, C. Yoshina-Ishii, S. D. Taylor, V. Santhakumar, Tetrahedron Lett., 1999, 40, 2669
30. J. A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R. S. Brown, R. A. Batey, Tetrahedron, 2005, 61, 7153
31. M. C. Whisler, M. MacNeil, V. Snieckus, P. Beak, Angew. Chem., Int. Ed., 2004, 43, 2207
32. J. Clayden, Organolithiums selectivity for synthesis, Pergamon, Oxford, 2003, pp. 249-256
33. J. Clayden, J. Dufour, D. Grainger, M. Helliwell, J. Am. Chem. Soc., 2007, 129, 7488
34. J. Clayden, M. Donnard, J. Lefranc, A. Minassi, D. J. Tetlow, J. Am. Chem. Soc., 2010, 132, 6624
35. J. Clayden, U. Hennecke, Org. Lett., 2008, 10, 3567
36. R. Bach, J. Clayden, U. Hennecke, Synlett, 2009, 421
37. T. J. Snape, Chem. Soc. Rev., 2008, 37, 2452
38. R. W. Hoffmann, R. K. Dress, T. Ruhland, Angew. Chem., Int. Ed. Engl., 1993, 32, 1467
39. R. W. Hoffmann, R. K. Dress, T. Ruhland, A. Wenzel, Chem. Ber., 1995, 128, 861
40. B. Kaiser, D. Hoppe, Angew. Chem., Int. Ed. Engl., 1995, 34, 323