The homologous conjugate addition of thiols to electron-deficient cyclopropanes catalyzed by a calcium(II) complex

Tetrahedron Letters

Volumn 54, Issue 44, 2013, Pages 5889-5891

  Braun, Caroline M ^a   Shema, Alyssa M ^a   Dulin, Callie C ^a   Nolin, Kristine A ^a  

^a UNIVERSITY OF RICHMOND   (United States)

Author keywords

Calcium catalysis; Cyclopropanes; Homologous conjugate addition; Thiol addition

Indexed keywords

CALCIUM ION; CYCLOPROPANE DERIVATIVE; THIOL DERIVATIVE;

ACID BASE BALANCE; ARTICLE; CATALYSIS; CONJUGATE; CYCLOADDITION; ELECTRON; NUCLEOPHILICITY; PROTON TRANSPORT; REACTION OPTIMIZATION; RING OPENING;

EID: 84884868764     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.08.102     Document Type: Article

References (39)

1. S. Danishefsky, and R.K. Singh J. Am. Chem. Soc. 97 1975 3239 3241
2. H. Wong, M. Hon, C. Tse, Y. Yip, J. Tanko, and T. Hudlicky Chem. Rev. 89 1989 165 198
3. H. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
4. H.U. Reissig Top. Curr. Chem. 144 1988 73 135
5. M. Yu, and B.L. Pagenkopf Tetrahedron 61 2005 321 347
6. S. Danishefsky, and G. Rovnyak J. Org. Chem. 39 1974 2924 2925
7. C.-S. Lee, K.-I. Lee, and A.D. Hamilton Tetrahedron Lett. 42 2001 211 213
8. Y. Yang, and M. Shi J. Org. Chem. 70 2005 10082 10085
9. M.R. Emmett, H.K. Grover, and M.A. Kerr J. Org. Chem. 77 2012 6634 6637
10. O. Lifchits, D. Alberico, I. Zakharian, and A.B. Charette J. Org. Chem. 73 2008 6838 6840
11. D.B. England, T.D.O. Kuss, R.G. Keddy, and M.A. Kerr J. Org. Chem. 66 2001 4704 4709
12. A.F.G. Goldberg, N.R. O'Connor, R.A. Craig II, and B.M. Stoltz Org. Lett. 14 2012 5314 5317
13. M.A. Kerr, and R.G. Keddy Tetrahedron Lett. 40 1999 5671 5675
14. P.D. Pohlhaus, S.D. Sanders, A.T. Parsons, W. Li, and J.S. Johnson J. Am. Chem. Soc. 130 2008 8642 8650
15. I.S. Young, and M.A. Kerr Angew. Chem., Int. Ed. 42 2003 3023 3026
16. M.P. Sibi, Z. Ma, and C.P. Jasperse J. Am. Chem. Soc. 127 2005 5764 5765
17. H.K. Grover, T.P. Lebold, and M.A. Kerr Org. Lett. 13 2011 220 223
18. S. Haubenreisser, P. Hensenne, S. Schröder, and M. Niggemann Org. Lett. 15 2013 2262 2265
19. A.T. Parsons, and J.S. Johnson J. Am. Chem. Soc. 131 2009 3122 3123
20. H. Xiong, H. Xu, S. Liao, Z. Xie, and Y. Tang J. Am. Chem. Soc. 135 2013 7851 7854
21. F. de Nanteuil, J. Loup, and J. Waser Org. Lett. 15 2013 3738 3741
22. S.M. Wales, M.M. Walker, and J.S. Johnson Org. Lett. 15 2013 2558 2561
23. R.A. Novikov, V.P. Timofeev, and Y.V. Tomilov J. Org. Chem. 77 2012 5993 6006
24. C. Carson, I. Young, and M. Kerr Synthesis 2008 2008 485 489
25. F.A. Coton, G. Wilkinson, and P.L. Gaus Basic Inorganic Chemistry 3rd ed. 1995 Wiley New York
26. M. Crimmin, A. Barrett, M. Hill, and P. Hitchcock Organometallics 26 2007 2953 2956
27. M.R. Crimmin, I.J. Casely, and M.S. Hill J. Am. Chem. Soc. 127 2005 2042 2043
28. F. Buch, and S. Harder Organometallics 26 2007 5132 5135
29. S. Saito, and S. Kobayashi J. Am. Chem. Soc. 128 2006 8704 8705
30. G. Kumaraswamy, M. Sastry, and N. Jena Tetrahedron Lett. 42 2001 8515 8517
31. W. Zheng, Z. Zhang, M.J. Kaplan, and J.C. Antilla J. Am. Chem. Soc. 133 2011 3339 3341
32. S. Saito, T. Tsubogo, and S. Kobayashi J. Am. Chem. Soc. 129 2007 5364 5365
33. S. Saito, T. Tsubogo, and S. Kobayashi Chem. Commun. 2007 1236 1237
34. Thiol and thiolate addition to electron-deficient cyclopropanes: C.-S. Lee, K.-I. Lee, and A.D. Hamilton Tetrahedron Lett. 42 2001 211 213
35. B. Hanquet, R. Guilard, and Y. Dusausoy J. Chem. Soc., Perkin Trans. 1 1985 983 989
36. P. Müller, and D. Riegert Tetrahedron 61 2005 4373 4379
37. H. Shao, S. Ekthawatchai, C.S. Chen, S.-H. Wu, and W. Zou J. Org. Chem. 70 2005 4726 4734
38. J.M. Stewart, and H.H. Westberg J. Org. Chem. 30 1965 1951 1955
39. K. Watanabe, N. Yamagiwa, and Y. Torisawa Org. Proccess Res. Dev. 11 2007 251 258